CN115915808A

CN115915808A - Light emitting device and method of manufacturing the same

Info

Publication number: CN115915808A
Application number: CN202211081492.2A
Authority: CN
Inventors: 金世勋; 李昌熙; 河在国; 姜鎭求; 具永谟; 金英一; 金志允
Original assignee: Samsung Display Co Ltd
Current assignee: Samsung Display Co Ltd
Priority date: 2021-09-28
Filing date: 2022-09-06
Publication date: 2023-04-04
Also published as: US20230135917A1; KR20230045756A

Abstract

Light emitting devices and methods of manufacturing light emitting devices are provided. The light emitting device includes: a substrate; a cathode on the substrate; an anode on the cathode; and an organic layer disposed between the cathode and the anode and including an emission layer. The organic layer includes: an electron transport region between the emissive layer and the cathode; and a hole transport region between the emission layer and the anode, wherein the hole transport region includes a first compound including a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof, wherein formula 1, formula 2, and formula 5 are respectively the same as described herein.

Description

Light emitting device and method of manufacturing the same

Cross Reference to Related Applications

This application claims priority and benefit of korean patent application No. 10-2021-0128342, filed on 28.9.2021, which is hereby incorporated by reference for all purposes as if fully set forth herein.

Technical Field

Embodiments of the invention generally relate to light emitting devices and methods of making light emitting devices.

Background

The organic light emitting device is a self-emission device having a wide viewing angle, a high contrast ratio, a short response time, and excellent characteristics in terms of luminance, driving voltage, and response speed, compared to the related art device.

In one example, the organic light emitting device includes an organic emission layer between an anode and a cathode, and holes and electrons are injected from the anode and the cathode, respectively, to the organic emission layer. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.

In another example, quantum dots may be used as materials for performing various optical functions (e.g., a light conversion function, a light emission function, and the like) in optical members and various electronic devices. The quantum dots are nanoscale semiconductor nanocrystals having a quantum confinement effect, and can have different energy band gaps by adjusting the size and composition of the nanocrystals, and thus can emit light of various emission wavelengths.

The above information disclosed in this background section is only for background understanding of the inventive concept and, therefore, it may contain information that does not constitute prior art.

Disclosure of Invention

One or more inventive concepts consistent with one or more embodiments include a light emitting device having high efficiency and long life and a method of manufacturing the same.

Additional features of the inventive concept will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the inventive concept.

According to one or more embodiments, a light emitting device includes: a substrate; a cathode disposed on the substrate; an anode facing the cathode; and an organic layer disposed between the cathode and the anode and including an emission layer, wherein the organic layer includes: an electron transport region disposed between the emission layer and the cathode; and a hole transport region between the emissive layer and the anode, and the hole transport region includes: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof;

formula 1

Formula 1-1

Formula 2

N ₃ -(Ar ₂₁ ) _n21 -(L ₂₁ ) _a21 -(Ar ₂₂ ) _n22 -N ₃

Formula 5

N ₃ -(Ar ₅₁ ) _n51 -(L ₅₁ ) _a51 -(Ar ₅₂ ) _n52 -N ₃

Wherein, in formula 1, formula 1-1, formula 2 and formula 5,

Ar ₁₁ to Ar ₁₃ 、Ar ₂₁ 、Ar ₂₂ 、Ar ₅₁ And Ar ₅₂ Each independently of the others being a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

n11 to n13, n21, n22, n51 and n52 are each independently an integer from 1 to 10,

L ₁₁ and L ₂₁ Each independently a single bond, — C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b )-*'、*-C(＝O)-*'、*-C(＝S)-*'、*-C≡C-*'、*-B(R _1a )-*'、*-N(R _1a )-*'、*-O-*'、*-P(R _1a )-*'、*-Si(R _1a )(R _1b )-*'、*-P(＝O)(R _1a )-*'、*-S-*'、*-S(＝O)-*'、*-S(＝O) ₂ -' or-Ge (R) _1a )(R _1b )-*'，

L ₅₁ Is a first repeating unit represented by formula 1,

a11, a21 and a51 are each independently an integer from 1 to 20,

R ₁₁ is a group represented by the formula 1-1, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic group, i) R ₁₂ Is a binding site to an adjacent atom in formula 1, and R ₁₃ Is hydrogen, or ii) R ₁₂ Is hydrogen, and R ₁₃ Are binding sites to adjacent atoms in formula 1,

R ₁₄ 、R ₁₅ 、R _1a and R _1b Each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylthio, -C (Q) ₁ )(Q ₂ )(Q ₃ )、-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N(Q ₁ )(Q ₂ )、-B(Q ₁ )(Q ₂ )、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ )，

* And each indicates a binding site to an adjacent atom, and

R _10a and Q ₁ To Q ₃ Respectively as described herein.

According to one or more embodiments, a light emitting device includes: a substrate; a cathode disposed on the substrate; an anode facing the cathode; x light-emitting units between the cathode and the anode; and x-1 charge generation layers each disposed between two adjacent light emitting units among the x light emitting units and including an n-type charge generation layer and a p-type charge generation layer, wherein x is an integer of 2 or more, each of the x light emitting units includes an electron transport region, an emission layer, and a hole transport region sequentially disposed from the cathode, and the hole transport region includes: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof;

wherein, formula 1 and formula 2 may be the same as described herein, respectively.

According to one or more embodiments, a method of manufacturing a light emitting device includes: forming a cathode on a substrate; forming a first organic layer between the cathode and the anode; forming a second organic layer between the first organic layer and the anode; and forming a third organic layer between the second organic layer and the anode, wherein forming the third organic layer is performed by a solution method using a composition comprising: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof; wherein, formula 1, formula 2, and formula 5 may be the same as described herein, respectively.

It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are intended to provide further explanation of the invention as claimed.

Drawings

The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the inventive concept.

Fig. 1 and 2 are views each schematically showing the structure of a light emitting device according to an embodiment constructed according to the principles of the present invention.

Fig. 3 and 4 are each a diagram schematically showing the structure of an electronic apparatus according to an embodiment.

Detailed Description

In the following description, for purposes of explanation, numerous specific details are set forth in order to provide a thorough understanding of various embodiments or implementations of the invention. As used herein, "embodiments" and "embodiments" are interchangeable words, which are non-limiting examples of devices or methods that employ one or more of the inventive concepts disclosed herein. It may be evident, however, that the various embodiments may be practiced without these specific details or with one or more equivalent arrangements. In other instances, well-known structures and devices are shown in block diagram form in order to avoid unnecessarily obscuring the various embodiments. Moreover, the various embodiments may be different, but not necessarily exclusive. For example, the particular shapes, configurations and characteristics of the embodiments may be used or practiced in another embodiment without departing from the inventive concept.

The embodiments shown, unless otherwise indicated, are to be understood as providing illustrative features of varying detail for some ways in which the inventive concept may be practiced. Thus, unless otherwise specified, features, components, modules, layers, films, panels, regions, and/or aspects and the like (hereinafter individually or collectively referred to as "elements") of the various embodiments may be otherwise combined, separated, interchanged, and/or rearranged without departing from the inventive concepts.

The use of cross-hatching and/or shading in the figures is generally provided to clarify the boundaries between adjacent elements. Thus, unless otherwise specified, the presence or absence of cross-hatching or shading does not convey or indicate any preference or requirement for particular materials, material properties, sizes, proportions, commonality between illustrated elements, and/or any other characteristic, attribute, property, etc., of an element. Moreover, in the drawings, the size and relative sizes of elements may be exaggerated for clarity and/or descriptive purposes. While embodiments may be practiced differently, the specific order of processing may be performed differently than described. For example, two processes described in succession may be executed substantially concurrently or in the reverse order to that described. Moreover, like reference numerals designate like elements.

When an element such as a layer is referred to as being "on," "connected to" or "coupled to" another element or layer, it can be directly on, connected or coupled to the other element or layer or intervening elements or layers may be present. However, when an element or layer is referred to as being "directly on," "directly connected to" or "directly coupled to" another element or layer, there are no intervening elements or layers present. To this end, the term "coupled" may refer to a physical, electrical, and/or fluid connection, with or without intervening elements. For the purposes of this disclosure, "at least one of X, Y, and Z" and "at least one selected from the group consisting of X, Y, and Z" may be construed as X only, Y only, Z only, or any combination of two or more of X, Y, and Z, such as, for example, XYZ, XYY, YZ, and ZZ. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.

Although the terms first, second, etc. may be used herein to describe various types of elements, these elements should not be limited by these terms. These terms are used to distinguish one element from another. Thus, a first element discussed below could be termed a second element without departing from the teachings of the present disclosure.

Spatially relative terms, such as "below," "lower," "above," "upper," "above," "higher," "side" (e.g., as in a "sidewall") and the like, may be used herein for descriptive purposes and thus to describe one element's relationship to another element or elements as illustrated in the figures. Spatially relative terms are intended to encompass different orientations of the device in use, operation, and/or manufacture in addition to the orientation depicted in the figures. For example, if the device in the figures is turned over, elements described as "below" or "beneath" other elements or features would then be oriented "above" the other elements or features. Thus, the term "below" can encompass both an orientation of above and below. Further, the devices may be otherwise oriented (e.g., rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particular embodiments and is not intended to be limiting. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, the terms "comprises," "comprising," "including," "includes" and/or "including," when used in this specification, specify the presence of stated features, integers, steps, operations, elements, components, and/or groups thereof, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof. It is also noted that, as used herein, the terms "substantially," "about," and other similar terms are used as terms of approximation and not as terms of degree, and thus, are utilized to interpret an inherent deviation of a measured value, a calculated value, and/or a provided value as would be recognized by one of ordinary skill in the art.

Various embodiments are described herein with reference to cross-sectional illustrations and/or exploded illustrations that are schematic illustrations of idealized embodiments and/or intermediate structures. Thus, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments disclosed herein should not be construed as limited to the shapes of the regions specifically illustrated, but are to include deviations in shapes that result, for example, from manufacturing. In this manner, the regions illustrated in the figures may be schematic in nature and the shapes of these regions may not reflect the actual shape of a region of a device and, thus, are not necessarily intended to be limiting.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure belongs. Terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[ description of FIG. 1]

Hereinafter, a light emitting device 10 according to an embodiment constructed according to the principles of the present invention will be described with reference to fig. 1.

Referring to fig. 1, a light emitting device 10 according to an embodiment includes: a substrate 100; a cathode 110 disposed on the substrate 100; an anode 150 facing the cathode 110; and an organic layer 160 disposed between the cathode 110 and the anode 150 and including an emission layer 130, wherein the organic layer 160 includes: an electron transport region 120 disposed between the emission layer 130 and the cathode 110; and a hole transport region 140 between the emissive layer 130 and the anode 150.

[ substrate 100]

As for use as the substrate 100, any substrate commonly used in the related art may be used, and the substrate 100 may be an inorganic substrate or an organic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling property, and water resistance.

In an embodiment, as the substrate 100, a glass substrate or a plastic substrate may be used. In one or more embodiments, the substrate 100 may be a flexible substrate, and may include, for example, a plastic having excellent heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

[ cathode 110]

The cathode 110 on the substrate 100 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In an embodiment, when the cathode 110 is a transmissive electrode, a material forming the cathode 110 may include Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) ₂ ) Zinc oxide (ZnO), or any combination thereof. In one or more embodiments, when the cathode 110 is a semi-transmissive electrode or a reflective electrode, a material forming the cathode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

The cathode 110 may have a single layer structure composed of a single layer or a multi-layer structure including two or more layers. For example, the cathode 110 may have a three-layer structure of ITO/Ag/ITO.

[ Electron transport region 120]

An electron transport region 120 is disposed on the cathode 110.

The electron transport region 120 may have: i) A single layer structure consisting of a single layer consisting of a single material; ii) a single layer structure consisting of a single layer, the single layer consisting of a plurality of different materials; or iii) a multilayer structure comprising a plurality of layers comprising different materials.

The electron transport region 120 may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transport region 120 may have a structure of an electron injection layer/electron transport layer, a structure of a hole injection layer/electron transport layer/electron blocking layer, a structure of an electron injection layer/electron transport layer/electron control layer, or a structure of an electron injection layer/electron transport layer/buffer layer, wherein the constituent layers of each structure are sequentially stacked from the cathode 110.

The electron transport region 120 can include a metal oxide, and the metal in the metal oxide can include Zn, ti, zr, sn, W, ta, ni, mo, cu, mg, co, mn, Y, al, or any combination thereof. In addition, the electron transport region 120 may include a metal sulfide, such as CuSCN and the like.

The electron transport region 120 (e.g., an electron injection layer or an electron transport layer included in the electron transport region 120) may include a third compound represented by formula 3:

formula 3

M _p O _q

Wherein, in the formula 3,

m may be Zn, ti, zr, sn, W, ta, ni, mo, cu or V, and

p and q may each independently be an integer from 1 to 5.

The third compound may be represented by formula 3-1:

formula 3-1

Zn _(1-r) M' _r O

Wherein, in the formula 3-1,

m' can be Mg, co, ni, zr, mn, sn, Y, al, or any combination thereof, and

r may be a number greater than 0 and equal to or less than 0.5.

In an embodiment, the electron transport region 120 may include ZnO or ZnMgO.

In one or more embodiments, the electron transport region 120 may include a second compound represented by formula 2. The second compound represented by formula 2 may be the same as described herein.

[ emitting layer 130]

When the light emitting device 10 is a full color light emitting device, the emission layer 130 may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer according to sub-pixels. In an embodiment, the emission layer 130 may have a stacked structure in which two or more layers among a red emission layer, a green emission layer, and a blue emission layer are in contact with or separated from each other to emit white light. In one or more embodiments, emissive layer 130 may have the following structure: two or more materials among the red light emitting material, the green light emitting material, and the blue light emitting material are mixed with each other in a single layer to emit white light.

In an embodiment, the emission layer 130 may include a host and a dopant. The dopant may include a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

The amount of the dopant included in the emission layer 130 may range from about 0.01 parts by weight to about 15 parts by weight, based on 100 parts by weight of the host.

In one or more embodiments, emissive layer 130 may comprise quantum dots.

In one or more embodiments, the emissive layer 130 can include a delayed fluorescence material. The delayed fluorescent material may act as a host or dopant in the emission layer 130.

The thickness of the emissive layer 130 may be about

To about->

(e.g., about->

To about>

) Within the range of (1). When the thickness of the emission layer 130 is within these ranges, excellent light emission characteristics may be obtained without significantly increasing the driving voltage.

[ subject ]

In embodiments, the subject may include a compound represented by formula 301:

formula 301

[Ar ₃₀₁ ] _xb11 -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb21

Wherein, in the formula 301,

Ar ₃₀₁ and L ₃₀₁ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

xb11 can be 1,2 or 3,

xb1 may be an integer from 0 to 5,

R ₃₀₁ can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, -Si (Q) ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ )、-N(Q ₃₀₁ )(Q ₃₀₂ )、-B(Q ₃₀₁ )(Q ₃₀₂ )、-C(＝O)(Q ₃₀₁ )、-S(＝O) ₂ (Q ₃₀₁ ) or-P (= O) (Q) ₃₀₁ )(Q ₃₀₂ )，

xb21 can be an integer from 1 to 5, and

Q ₃₀₁ to Q ₃₀₃ Can each be related to Q ₁ The description is the same.

For example, when xb11 in formula 301 is 2 or more, two or more Ar ₃₀₁ May be bonded together by a single bond.

In one or more embodiments, the subject may include a compound represented by formula 301-1, a compound represented by formula 301-2, or any combination thereof:

formula 301-1:

formula 301-2:

in formulae 301-1 and 301-2,

ring A ₃₀₁ To ring A ₃₀₄ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

X ₃₀₁ can be O, S, N- [ (L) ₃₀₄ ) _xb4 -R ₃₀₄ ]、C(R ₃₀₄ )(R ₃₀₅ ) Or Si (R) ₃₀₄ )(R ₃₀₅ )，

xb22 and xb23 can each independently be 0, 1 or 2,

L ₃₀₁ xb1 and R ₃₀₁ May each be the same as described herein,

L ₃₀₂ to L ₃₀₄ Can each independently relate to L ₃₀₁ The same as that described above is true of,

xb2 to xb4 may each independently be the same as described for xb1, and

R ₃₀₂ to R ₃₀₅ And R ₃₁₁ To R ₃₁₄ Can each be related to R ₃₀₁ The same is described.

In one or more embodiments, the host may include an alkaline earth metal complex, a late transition metal complex, or any combination thereof. In one or more embodiments, the host may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.

In one or more embodiments, the host can include one of compound H1 through compound H126, 9, 10-bis (2-naphthyl) Anthracene (ADN), 2-methyl-9, 10-bis (naphthalen-2-yl) anthracene (MADN), 9, 10-bis- (2-naphthyl) -2-tert-butyl-anthracene (TBADN), 4 '-bis (N-carbazolyl) -1,1' -biphenyl (CBP), 1, 3-bis-9-carbazolylbenzene (mCP), 1,3, 5-tris (carbazol-9-yl) benzene (TCP), or any combination thereof:

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[ phosphorescent dopant ]

In embodiments, the phosphorescent dopant may include at least one transition metal as a central metal.

The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

The phosphorescent dopant may be electrically neutral.

In one or more embodiments, the phosphorescent dopant may include an organometallic compound represented by formula 401:

formula 401

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

Formula 402

In the case of the formulas 401 and 402,

m can be a transition metal (e.g., iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

L ₄₀₁ may be a ligand represented by formula 402, and xc1 may be 1,2, or 3, wherein, when xc1 is 2 or greater, two or more L' s ₄₀₁ Which may be the same as or different from each other,

L ₄₀₂ can be an organic ligand, and xc2 can be 0, 1,2,3, or 4, wherein, when xc2 is 2 or greater, two or more L' s ₄₀₂ Which may be the same as or different from each other,

X ₄₀₁ and X ₄₀₂ May each independently be nitrogen or carbon,

ring A ₄₀₁ And ring A ₄₀₂ May each independently be C ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ A heterocyclic group,

T ₄₀₁ can be a single bond, — O-, — S-, — C (= O) -, — N (Q) ₄₁₁ )-*'、*-C(Q ₄₁₁ )(Q ₄₁₂ )-*'、*-C(Q ₄₁₁ )＝C(Q ₄₁₂ )-*'、*-C(Q ₄₁₁ ) Or = C =',

X ₄₀₃ and X ₄₀₄ Can each independently be a chemical bond (e.g., covalent or coordinate), O, S, N (Q) ₄₁₃ )、B(Q ₄₁₃ )、P(Q ₄₁₃ )、C(Q ₄₁₃ )(Q ₄₁₄ ) Or Si (Q) ₄₁₃ )(Q ₄₁₄ )，

Q ₄₁₁ To Q ₄₁₄ Can each be related to Q ₁ The same as that described above is true of,

R ₄₀₁ and R ₄₀₂ Can be each independently hydrogen,Deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₂₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₂₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, -Si (Q) ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ )、-N(Q ₄₀₁ )(Q ₄₀₂ )、-B(Q ₄₀₁ )(Q ₄₀₂ )、-C(＝O)(Q ₄₀₁ )、-S(＝O) ₂ (Q ₄₀₁ ) or-P (= O) (Q) ₄₀₁ )(Q ₄₀₂ )，

Q ₄₀₁ To Q ₄₀₃ Can each be related to Q ₁ The same as that described above is true of,

xc11 and xc12 may each independently be an integer from 0 to 10, and

each of @and @' in formula 402 indicates a binding site to M in formula 401.

For example, in formula 402, i) X ₄₀₁ May be nitrogen, and X ₄₀₂ Can be carbon, or ii) X ₄₀₁ And X ₄₀₂ May be nitrogen.

In embodiments, when xc1 in formula 401 is 2 or greater, two or more L ₄₀₁ In which two rings A ₄₀₁ Optionally via T as a linking group ₄₀₂ Are bonded to each other; and two or more of L ₄₀₁ In which two rings A ₄₀₂ Optionally via T as a linking group ₄₀₃ Bonded to each other (see compound PD1 to compound PD4 and compound PD 7). T is a unit of ₄₀₂ And T ₄₀₃ Can each be related to T ₄₀₁ The description is the same.

In formula 401, L ₄₀₂ May be an organic ligand. For example, L ₄₀₂ May include a halogen group, a diketone group (e.g., an acetylacetone group), a carboxylic acid group (e.g., a picolinate group), -C (= O), an isonitrile group, -a CN group, a phosphorous group (e.g., a phosphine group, a phosphite group, and the like), or any combination thereof.

The phosphorescent dopant may include, for example, one or any combination of compound PDl to compound PD 39:

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[ fluorescent dopant ]

The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

For example, the fluorescent dopant may include a compound represented by formula 501:

formula 501

In the formula 501,

Ar ₅₀₁ 、L ₅₀₁ to L ₅₀₃ 、R ₅₀₁ And R ₅₀₂ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

xd1 to xd3 may each independently be 0, 1,2 or 3, and

xd4 may be 1,2,3,4, 5 or 6.

For example, ar in formula 501 ₅₀₁ There may be three or more monocyclic groups fused together (e.g., anthracene base,

A base,Pyrenyl and the like).

For example, xd4 in equation 501 may be 2.

In one or more embodiments, the fluorescent dopant may include: one of compound FD1 to compound FD 38; DPVBi; DPAVBi; or any combination thereof:

/>

/>

[ delayed fluorescence Material ]

The emission layer 130 may include a delayed fluorescence material.

As described herein, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescence by a delayed fluorescence emission mechanism.

The delayed fluorescence material included in the emission layer 130 may serve as a host or a dopant according to the type of other materials included in the emission layer 130.

In embodiments, the difference between the triplet level (eV) of the delayed fluorescence material and the singlet level (eV) of the delayed fluorescence material may be about 0eV or more and about 0.5eV or less. When the difference between the triplet level (eV) of the delayed fluorescent material and the singlet level (eV) of the delayed fluorescent material satisfies the above range, the up-conversion of the delayed fluorescent material from the triplet state to the singlet state can effectively occur, so that the light emitting efficiency or the like of the light emitting device 10 can be improved.

For example, the delayed fluorescence material may include: i) Including at least one electron donor (e.g., pi electron rich C) ₃ -C ₆₀ Cyclic groups and the like, such as carbazolyl) and at least one electron acceptor (e.g., sulfoxide group, cyano group, nitrogen-containing C lacking π electrons ₁ -C ₆₀ Cyclic groups and the like); and ii) comprises C ₈ -C ₆₀ Materials of polycyclic radicals, in C ₈ -C ₆₀ In the polycyclic group, two or more cyclic groups are condensed while sharing boron (B).

Examples of delayed fluorescence materials are at least one of compound DF1 to compound DF 9:

[ Quantum dots ]

The emission layer 130 may include quantum dots.

The term "quantum dot" as used herein refers to a crystal of a semiconductor compound, and may include any material capable of emitting light of various emission wavelengths depending on the size of the crystal.

The diameter of the quantum dots can be in the range of, for example, about 1nm to about 10 nm.

The quantum dots can be synthesized by wet chemical methods, metal organic chemical vapor deposition methods, molecular beam epitaxy methods, or any method similar thereto.

The wet chemistry process is a process comprising: the precursor material is mixed with an organic solvent, and then quantum dot particle crystals are grown. When the crystal grows, the organic solvent naturally acts as a dispersant to coordinate on the surface of the quantum dot crystal and control the growth of the crystal, so that the growth of the quantum dot particle can be controlled through a process that is less costly and easier than a vapor deposition method such as Metal Organic Chemical Vapor Deposition (MOCVD) or Molecular Beam Epitaxy (MBE).

The quantum dots may include: group II-VI semiconductor compounds; a group III-V semiconductor compound; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; a group IV element or compound; or any combination thereof.

Examples of the group II-VI semiconductor compounds are: binary compounds such as CdSe, cdTe, znS, znSe, znTe, znO, hgS, hgSe, hgTe, mgSe, mgS, and the like; ternary compounds such as CdSeS, cdSeTe, cdSTe, znSeS, znSeTe, znSTe, hgSeS, hgSeTe, hgSTe, cdZnS, cdZnSe, cdZnTe, cdHgS, cdHgSe, cdHgTe, hgZnS, hgZnSe, hgZnTe, mgZnSe, mgZnS and the like; quaternary compounds such as CdZnSeS, cdZnSeTe, cdHgSeS, cdHgSeTe, cdHgSTe, hgZnSeS, hgZnSeTe, and the like; or any combination thereof.

Examples of group III-V semiconductor compounds are: binary compounds such as GaN, gaP, gaAs, gaSb, alN, alP, alAs, alSb, inN, inP, inAs, inSb, and the like; ternary compounds such as GaNP, gaNAs, gaNSb, gaAs, gaPSb, alNP, alNAs, alNSb, alPAs, alPSb, inGaP, inNP, inAlP, inNAs, inNSb, inPAs, inPSb, and the like; quaternary compounds such as GaAlNP, gaAlNAs, gaAlNSb, gaAlPAs, gaAlPSb, gainp, gaInNAs, gainsb, gaInPAs, gaInPSb, inAlNSb, inalnnas, inAlNSb, inalnpas, inAlNSb, and the like; or any combination thereof. The group III-V semiconductor compound may further include a group II element. Examples of group III-V semiconductor compounds further comprising a group II element are InZnP, inGaZnP, inAlZnP, and the like.

Examples of group III-VI semiconductor compounds are: binary compounds, such as GaS, gaSe, ga ₂ Se ₃ 、GaTe、InS、InSe、In ₂ S ₃ 、In ₂ Se ₃ Intee, and the like; ternary compounds, such as InGaS ₃ 、InGaSe ₃ And the like; or any combination thereof.

Examples of group I-III-VI semiconductor compounds are: ternary compounds, such as AgInS, agInS ₂ 、CuInS、CuInS ₂ 、CuGaO ₂ 、AgGaO ₂ 、AgAlO ₂ And the like; or any combination thereof.

Examples of group IV-VI semiconductor compounds are: binary compounds such as SnS, snSe, snTe, pbS, pbSe, pbTe, and the like; ternary compounds such as SnSeS, snSeTe, snSTe, pbSeS, pbSeTe, pbSTe, snPbS, snPbSe, snPbTe and the like; quaternary compounds such as SnPbSSe, snPbSeTe, snPbSTe, and the like; or any combination thereof.

The group IV element or compound may include: single element materials such as Si, ge, and the like; binary compounds such as SiC, siGe, and the like; or any combination thereof.

Each element included in the multi-element compound (such as binary compounds, ternary compounds, and quaternary compounds) may be present in the particle in a uniform concentration or a non-uniform concentration.

The quantum dots may have a single structure or a double core-shell structure. In the case where the quantum dots have a single structure, the concentration of each element included in the respective quantum dots may be uniform. For example, the material included in the core and the material included in the shell may be different from each other.

The shell of the quantum dot may serve as a protective layer preventing chemical degradation of the core to maintain semiconductor properties and/or as a charging layer imparting electrophoretic properties to the quantum dot. The shell may be a single layer or multiple layers. The interface between the core and the shell may have a concentration gradient in which the concentration of the element present in the shell decreases toward the center of the core.

Examples of shells of quantum dots are metal oxides, metalloid oxides, semiconductor compounds, or any combination thereof. Examples of metal oxides, metalloid oxides or non-metal oxides are: binary compounds, such as SiO ₂ 、Al ₂ O ₃ 、TiO ₂ 、ZnO、MnO、Mn ₂ O ₃ 、Mn ₃ O ₄ 、CuO、FeO、Fe ₂ O ₃ 、Fe ₃ O ₄ 、CoO、Co ₃ O ₄ NiO, and the like; ternary compounds, such as MgAl ₂ O ₄ 、CoFe ₂ O ₄ 、NiFe ₂ O ₄ 、CoMn ₂ O ₄ And the like; or any combination thereof. Examples of semiconducting compounds are: group II-VI semiconductor compounds, as described herein; a group III-V semiconductor compound; group III-VI semiconductor compounds; group I-III-VI semiconductorizationA compound; group IV-VI semiconductor compounds; or any combination thereof. Examples of semiconductor compounds are CdS, cdSe, cdTe, znS, znSe, znTe, znSeS, znTeS, gaAs, gaP, gaSb, hgS, hgSe, hgTe, inAs, inP, inGaP, inSb, alAs, alP, alSb, or any combination thereof.

The full width at half maximum (FWHM) of the emission wavelength spectrum of the quantum dot may be about 45 nanometers (nm) or less, for example, about 40nm or less, for example, about 30nm or less, and in these ranges, the color purity or the color reproducibility may be improved. In addition, since light emitted from the quantum dots is emitted in all directions, a wide viewing angle can be improved (e.g., an increased viewing angle can be obtained).

Furthermore, the quantum dots may specifically be spherical, pyramidal, multi-armed or cubic nanoparticles, nanotubes, nanowires, nanofibers or nanoplates.

Since the energy band gap can be adjusted by controlling the size of the quantum dot, light having various wavelength bands can be obtained from the emission layer including the quantum dot. Therefore, by using quantum dots of different sizes, light emitting devices that emit light of various wavelengths can be realized. In particular, the size of the quantum dots may be selected in consideration of emitting red, green and/or blue light. In addition, the size of the quantum dots may be configured to emit white light by combining various colors of light.

[ hole transport region 140]

The hole transport region 140 may have: i) A single layer structure consisting of a single layer consisting of a single material; ii) a monolayer structure consisting of a single layer consisting of a plurality of different materials; or iii) a multilayer structure comprising a plurality of layers comprising different materials.

The hole transport region 140 may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.

For example, the hole transport region 140 may include a multi-layer structure including a hole transport layer/hole injection layer structure, an emission auxiliary layer/hole transport layer structure, or an electron blocking layer/hole transport layer/hole injection layer structure, wherein the constituent layers of each structure are sequentially stacked from the emission layer 130.

The hole transport region 140 may include: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof:

formula 1

In formula 1, ar ₁₁ To Ar ₁₃ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group.

In embodiments, ar ₁₁ To Ar ₁₃ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₁₀ Cycloalkylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₁₀ Heterocycloalkylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₁₀ Cycloalkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₁₀ Heterocycloalkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heteroarylene, unsubstituted or substituted by at least one R _10a A substituted divalent non-aromatic fused polycyclic group, either unsubstituted or substituted with at least one R _10a Substituted divalent non-aromatic fused heteropolycyclic groupWherein R is _10a May be the same as described herein.

In one or more embodiments, ar ₁₁ To Ar ₁₃ May each independently be:

a single bond; or

Phenyl, naphthyl, anthryl, phenanthryl, benzo [9,10 ]]Phenanthryl, pyrenyl,

<xnotran> , ,1,2,3,4- , , , , (benzoborole), (benzophosphole), , (benzosilole), (benzogermole), , , , , , , , , , , , , 5- , 9H- -9- , 5,5- , , , , , , , , , , , , , , , , , , , , 5- , -9H- -9- , 5,5- , , , , , , , , , , </xnotran> Phenanthroline, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolylBenzimidazolyl, benzoxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl, or 5,6,7, 8-tetrahydroquinolinyl, each of which is unsubstituted or substituted with at least one R _10a Is substituted and

R _10a may be the same as described herein.

In one or more embodiments, ar ₁₁ To Ar ₁₃ May each independently be:

a single bond, phenylene, naphthalene or fluorene; or

Phenylene, naphthalene or fluorene, each of which is deuterated, C ₁ -C ₁₀ Alkyl, phenyl, or any combination thereof.

In one or more embodiments, ar ₁₁ To Ar ₁₃ May each independently be a single bond or a group represented by one of formula 1A-1 to formula 1A-13 and formula 1B-1 to formula 1B-10:

in formulae 1A-1 to 1A-13 and formulae 1B-1 to 1B-10,

R _1c and R _1d May each independently be hydrogen, deuterium, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

* And each indicates a binding site to an adjacent atom, and

R _10a may be the same as described herein.

For example, in the formulae 1B-1 to 1BIn-10, R _1c And R _1d May each independently be hydrogen, deuterium, C ₁ -C ₂₀ Alkyl radical, C ₂ -C ₂₀ Alkenyl radical, C ₂ -C ₂₀ Alkynyl, phenyl or naphthyl.

In formula 1, n11 to n13 may each independently be an integer from 1 to 10. In embodiments, the number of Ar is n11 ₁₁ Ar of n12 which may be the same or different from each other ₁₂ Ar, which may be the same or different from each other, in number n13 ₁₃ May be the same as or different from each other.

In embodiments, n11 to n13 may each independently be an integer from 1 to 3.

In formula 1, L ₁₁ Can be a single bond, -C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、

*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b )-*'、*-C(＝O)-*'、*-C(＝S)-*'、*-C≡C-*'、

*-B(R _1a )-*'、*-N(R _1a )-*'、*-O-*'、*-P(R _1a )-*'、*-Si(R _1a )(R _1b )-*'、

*-P(＝O)(R _1a )-*'、*-S-*'、*-S(＝O)-*'、*-S(＝O) ₂ -' or-Ge (R) _1a )(R _1b ) -, and' each indicate a binding site to an adjacent atom, and R _1a And R _1b May each be the same as described herein.

In an embodiment, L ₁₁ Can be-C (R) _1a )(R _1b ) -' or-O-.

In embodiments, from (L) ₁₁ ) _a11 The moiety represented may be a group represented by formula 1L:

in the case of the formula 1L,

n1L may be an integer from 0 to 10,

Z _1L can be hydrogen, deuterium, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at leastA R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, or unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ An arylthio group is a group selected from the group consisting of,

* And each indicates a binding site to an adjacent atom, and

R _10a may be the same as described herein.

In embodiments, n1L may be an integer from 2 to 5.

In embodiments, Z _1L Can be hydrogen, deuterium, C ₁ -C ₁₀ Alkyl or phenyl.

In embodiments, indicates a chemical bond with (Ar) in formula 1 ₁₃ ) _n13 The moiety represented or the binding site of N in formula 1, and indicates R in formula 1 ₁₁ The binding site of (1). That is, the bond shown in formula 1-1L can be formed:

formula 1-1L

In embodiments, a11 in formula 1 may be an integer from 1 to 20.

In one or more embodiments, a11 in formula 1 can be an integer from 3 to 10.

In embodiments, R in formula 1 ₁₁ May be a group represented by formula 1-1, unsubstituted or substituted with at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group.

In embodiments, R in formula 1 ₁₁ Can be as follows:

a group represented by formula 1-1; or

Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C ₁ -C ₂₀ Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,

<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , (benzimidazolyl), , , (benzosilolyl), , , , , , , , , , , , , , , , , , , , , , , , , (benzosilolocarbazolyl), , , , , , , : </xnotran> Deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxy, cyano, nitro, C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, cyclopentylCyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C ₁ -C ₂₀ Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl and/or pyrenyl>

<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , (benzosilolyl), , , , , , , , , , , , , , , , , , , , , , , , , (benzosilolocarbazolyl), , , -Si (Q </xnotran> ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-P(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ )、-P(＝O)(Q ₃₁ )(Q ₃₂ ) Or any combination thereof, and

Q ₃₁ to Q ₃₃ May be respectively the same as described herein.

In embodiments, R in formula 1 ₁₁ May be a group represented by formula 1-1:

formula 1-1

In the formula 1-1, i) R ₁₂ May be a binding site to an adjacent atom in formula 1, and R ₁₃ Can be hydrogen, or ii) R ₁₂ Can be hydrogen, and R ₁₃ May be a binding site to an adjacent atom in formula 1.

In embodiments, in formula 1-1, R ₁₄ And R ₁₅ Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylthio, -C (Q) ₁ )(Q ₂ )(Q ₃ )、-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N(Q ₁ )(Q ₂ )、-B(Q ₁ )(Q ₂ )、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ ) And is and

R _10a and Q ₁ To Q ₃ May be respectively the same as described herein.

In one or more embodiments, R ₁₄ And R ₁₅ May each independently be:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₁ -C ₂₀ Alkyl or C ₁ -C ₂₀ An alkoxy group;

C ₁ -C ₂₀ alkyl or C ₁ -C ₂₀ Alkoxy groups, each of which is substituted with: deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxy, cyano, nitro, C ₁ -C ₂₀ Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof;

cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₂₀ Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,

A group selected from the group consisting of a phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indenyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, a benzothiollyl group (benzoisiloyl), an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, an isothiazolyl group, a triazinyl, dibenzofuranyl, dibenzothienyl, dibenzothiapyrrolyl, benzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothienyl, naphthobenzothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiazolyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothiophenocarbazolyl (benzothiazolocarbazolyl), imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranylA furyl group, an azabicyclohexyl thienyl group, or an azabicyclooxyl group, each of which is unsubstituted or substituted with: deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxy, cyano, nitro, C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C ₁ -C ₂₀ Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl and/or on>

A group, pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, indenyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzothiophenyl (benzoisilol), isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, thiazolyl, and the like tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiazolyl, benzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenyl, dinaphthothiazolyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzothiophenocarbazolyl (benzothiazolocarbazolyl), imidazopyridinyl, imidazopyrimidinyl, -Si (Q) ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-P(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ )、-P(＝O)(Q ₃₁ )(Q ₃₂ ) Or any combination thereof; or

-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N[(L ₁₁ ) _b11 -Q ₁ ][(L ₁₂ ) _b12 -Q ₂ ]、-B[(L ₁₁ ) _b11 -Q ₁ ][(L ₁₂ ) _b12 -Q ₂ ]、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ ) And are each and every

Q ₁ To Q ₃ And Q ₃₁ To Q ₃₃ May each independently be:

-CH ₃ 、-CD ₃ 、-CD ₂ H、-CDH ₂ 、-CH ₂ CH ₃ 、-CH ₂ CD ₃ 、-CH ₂ CD ₂ H、-CH ₂ CDH ₂ 、-CHDCH ₃ 、-CHDCD ₂ H、-CHDCDH ₂ 、-CHDCD ₃ 、-CD ₂ CD ₃ 、-CD ₂ CD ₂ h or-CD ₂ CDH ₂ (ii) a Or

N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl or triazinyl, each of which is unsubstituted or substituted by: deuterium, C ₁ -C ₂₀ Alkyl, phenyl, biphenyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, or any combination thereof.

In one or more embodiments, R ₁₄ And R ₁₅ May each independently be:

hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₂₀ Alkyl or C ₁ -C ₂₀ An alkoxy group;

C ₁ -C ₂₀ alkyl or C ₁ -C ₂₀ Alkoxy, each of which is deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₁ -C ₂₀ Alkyl or any combination thereof;

a phenyl group or a naphthyl group,each of which is unsubstituted or is deuterated, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, or any combination thereof.

In formula 1, each of x and x' indicates a binding site to an adjacent atom.

In embodiments, the first compound may be one of compound 1-1 to compound 1-6:

compound 1-1

Compound 1-2

Compounds 1 to 3

Compounds 1 to 4

Compounds 1 to 5

Compounds 1 to 6

In one or more embodiments, the first compound may not include an azide group (-N) ₃ )。

In embodiments, the molecular weight of the first compound may be in the range of about 400 to about 20,000.

Formula 2

N ₃ -(Ar ₂₁ ) _n21 -(L ₂₁ ) _a21 -(Ar ₂₂ ) _n22 -N ₃

In embodiments, in formula 2, ar ₂₁ And Ar ₂₂ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group.

In one or more embodiments, in formula 2, ar ₂₁ And Ar ₂₂ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₁₀ Cycloalkylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₁₀ Heterocycloalkylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₁₀ Cycloalkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₁₀ Heterocycloalkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heteroarylene, unsubstituted or substituted by at least one R _10a A substituted divalent non-aromatic fused polycyclic group, either unsubstituted or substituted with at least one R _10a A substituted divalent non-aromatic fused heteropolycyclic group, and

R _10a may be the same as described herein.

In one or more embodiments, in formula 2, ar ₂₁ And Ar ₂₂ May each independently be:

a single bond; or

Phenyl, naphthyl, anthryl, phenanthryl, benzo [9,10 ]]Phenanthryl, pyrenyl,

<xnotran> , ,1,2,3,4- , , , , (benzoborole), (benzophosphole), , (benzosilole), (benzogermole), , , , , , , , , , , , , 5- , 9H- -9- , 5,5- , , , , , , , , , , , , , , , , , , , , 5- , -9H- -9- , 5,5- , , , , , , , , , , </xnotran> Phenanthrolinyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzoxadiazolyl, benzothiadiazolyl, 5,6,7, 8-tetrahydroisoquinolinyl or 5,6,7, 8-tetrahydroisoquinolinylQuinolyl, each of which is unsubstituted or substituted by at least one R _10a Is substituted and

R _10a may be the same as described herein.

phenylene or naphthalene; or

Phenylene or naphthalene, each of which is deuterium, -F or C ₁ -C ₁₀ And (3) alkyl substitution.

In one or more embodiments, in formula 2, ar ₂₁ And Ar ₂₂ Can each independently be

One of the groups of formulae 2A-1 to 2A-13:

in formulae 2A-1 to 2A-13,

Z ₁ can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro,

b11 may be an integer from 1 to 4,

b12 may be an integer from 1 to 6, and

* And each indicates a binding site to an adjacent atom.

In embodiments, in formula 2, n21 and n22 may each independently be an integer from 1 to 10.

In one or more embodiments, in formula 2, n21 and n22 may each independently be an integer from 1 to 3.

In embodiments, L in formula 1 ₁₁ Can be a single bond, -C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b )-*'、*-C(＝O)-*'、*-C(＝S)-*'、*-C≡C-*'、*-B(R _1a )-*'、*-N(R _1a )-*'、*-O-*'、*-P(R _1a )-*'、*-Si(R _1a )(R _1b )-*'、*-P(＝O)(R _1a )-*'、*-S-*'、*-S(＝O)-*'、*-S(＝O) ₂ -' or-Ge: (A) ((B))R _1a )(R _1b ) -' wherein each of denotes a binding site to an adjacent atom, and R _1a And R _1b May each be the same as described herein.

In one or more embodiments, L in formula 2 ₂₁ Can be a single bond, -C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b ) -, - (= O) -' or-O-.

In formula 2, a21 may be an integer from 1 to 20.

In one or more embodiments, L in formula 2 ₂₁ Can be a single bond, -C (R) _1a )(R _1b ) -, - (= O) -, or-, and a21 in formula 2 may be an integer from 1 to 10.

In embodiments, R _1a And R _1b Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylthio, -C (Q) ₁ )(Q ₂ )(Q ₃ )、-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N(Q ₁ )(Q ₂ )、-B(Q ₁ )(Q ₂ )、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ ) And is and

R _10a and Q ₁ To Q ₃ Can be respectively combined with the textThe same is described.

In one or more embodiments, R _1a And R _1b May each independently be:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C ₁ -C ₂₀ Alkyl or C ₁ -C ₂₀ An alkoxy group;

<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , (benzosilolyl), , , , , , , , , , , , , , , </xnotran>Naphthobenzothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophene, dinaphthothiazolyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzothiophenocarbazolyl (benzoilocarbazolyl), imidazopyridinyl, imidazopyrimidinyl, azafluorenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothienyl, or azadibenzothiapyrrolyl, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ Hydroxy, cyano, nitro, C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, terphenyl, C ₁ -C ₂₀ Alkylphenyl, naphthyl, fluorenyl, phenanthryl, anthracyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl and/or pyrenyl>

A phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indenyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a quinoxalyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuryl group, a benzothienyl group, a benzothiollyl group (benzoicilyl), an isobenzothiazolyl group benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, dibenzothiazolyl, benzofluorenyl, benzocarbazolyl, naphthobenzofuranyl, naphthobenzothiophenyl, dibenzofluorenyl, dibenzocarbazolyl, dinaphthofuranyl, dinaphthothiophenoyl, dinaphthothiazolyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolylBenzothiolocarbazolyl (benzothiazolocarbazolyl), imidazopyridinyl, imidazopyrimidinyl, -Si (Q) ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-P(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ )、-P(＝O)(Q ₃₁ )(Q ₃₂ ) Or any combination thereof; or

-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N[(L ₁₁ ) _b11 -Q ₁ ][(L ₁₂ ) _b12 -Q ₂ ]、-B[(L ₁₁ ) _b11 -Q ₁ ][(L ₁₂ ) _b12 -Q ₂ ]、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ ) And is and

Q ₁ to Q ₃ And Q ₃₁ To Q ₃₃ May each independently be:

In one or more embodiments, R _1a And R _1b May each independently be:

C ₁ -C ₂₀ alkyl or C ₁ -C ₂₀ Alkoxy, each of which is deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₁ -C ₂₀ Alkyl or any combination thereof; or

Phenyl or naphthyl, each of which is unsubstituted or is deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, or any combination thereof.

In embodiments, the second compound may be one of compound 2-1 to compound 2-3:

compound 2-1

Compound 2-2

Compound 2-3

Formula 5

N ₃ -(Ar ₅₁ ) _n51 -(L ₅₁ ) _a51 -(Ar ₅₂ ) _n52 -N ₃ 。

In embodiments, in formula 5, ar ₅₁ And Ar ₅₂ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group, and R _10a May be the same as described herein.

In one or more embodiments, ar ₅₁ And Ar ₅₂ May each independently be a single bond, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, and R _10a May be the same as described herein.

In embodiments, in formula 5, n51 and n52 may each independently be an integer from 1 to 10.

In formula 5, L ₅₁ May be a first repeating unit represented by formula 1:

formula 1

In formula 1, ar ₁₁ To Ar ₁₃ N11 to n13, L ₁₁ A11 and R ₁₁ May be respectively the same as described herein.

In embodiments, a51 in formula 5 may be an integer from 1 to 20.

In one or more embodiments, a51 in formula 5 may be an integer from 1 to 3.

In embodiments, the fifth compound may be represented by formula 5-1:

formula 5-1

In the formula 5-1, ar ₅₃ To Ar ₅₅ May each independently be a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene radical, not takenIs substituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group, and R _10a May be the same as described herein.

In embodiments, ar ₅₃ To Ar ₅₅ May each independently be:

a single bond, phenylene, naphthalene or fluorene; or alternatively

Phenylene, naphthalene or fluorene, each of which is deuterated, F, C ₁ -C ₁₀ Alkyl, phenyl, or any combination thereof.

In one or more embodiments, ar ₅₃ To Ar ₅₅ May each independently be a single bond or one of the groups represented by formula 5A-1 to formula 5A-13 and formula 5B-1 to formula 5B-10:

in the formulae 5A-1 to 5A-13 and 5B-1 to 5B-10,

R _5c and R _5d May each independently be hydrogen, deuterium, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

R ₅₁ 、R ₅₃ and R ₅₄ May each independently be deuterium, -F, -Cl, -Br, -I or C ₁ -C ₁₀ An alkyl group, a carboxyl group,

b51 may be an integer from 0 to 4,

b52 may be an integer from 0 to 6,

b53 and b54 may each independently be an integer from 0 to 3,

* And each indicates a binding site to an adjacent atom, and

R _10a may be the same as described herein.

For example, in the formulae 5B-1 to 5B-10, R _5c And R _5d Can be each independently hydrogen, deuterium, C ₁ -C ₂₀ Alkyl radical, C ₂ -C ₂₀ Alkenyl radical, C ₂ -C ₂₀ Alkynyl, phenyl or naphthyl.

In formula 5-1, n53 to n55 may each independently be an integer from 1 to 10. In embodiments, the number of Ar is n53 ₅₃ Ar of n54 which may be the same or different from each other ₅₄ Ar, which may be the same or different from each other, in a number of n55 ₅₅ May be the same as or different from each other.

In the formula 5-1, L ₅₂ Can be a single bond, -C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b )-*'、*-C(＝O)-*'、*-C(＝S)-*'、*-C≡C-*'、*-B(R _1a )-*'、*-N(R _1a )-*'、*-O-*'、*-P(R _1a )-*'、*-Si(R _1a )(R _1b )-*'、*-P(＝O)(R _1a )-*'、*-S-*'、*-S(＝O)-*'、*-S(＝O) ₂ -' or-Ge (R) _1a )(R _1b ) -, and' each indicate a binding site to an adjacent atom, and R _1a And R _1b Each may be the same as described herein.

In an embodiment, L ₅₂ Can be-C (R) _1a )(R _1b ) -' or-O-.

In embodiments, from (L) ₅₂ ) _a52 The moiety represented may be a group represented by formula 1L:

in the formula 1L, the compound represented by the formula,n1L and Z _1L May be respectively the same as described herein.

In the formula 5-1, R ₁₁ May be a group represented by formula 1-1, unsubstituted or substituted with at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group.

Formula 1-1

In the formula 1-1, i) R ₁₂ May be a binding site to an adjacent atom in formula 1, and R ₁₃ Can be hydrogen, or ii) R ₁₂ Can be hydrogen, and R ₁₃ Can be a binding site to an adjacent atom in formula 1.

In embodiments, in formula 1-1, R ₁₄ And R ₁₅ Can each independently be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylthio, -C (Q) ₁ )(Q ₂ )(Q ₃ )、-Si(Q ₁ )(Q ₂ )(Q ₃ )、-N(Q ₁ )(Q ₂ )、-B(Q ₁ )(Q ₂ )、-C(＝O)(Q ₁ )、-S(＝O) ₂ (Q ₁ ) or-P (= O) (Q) ₁ )(Q ₂ ) And is combined withAnd is

R _10a And Q ₁ To Q ₃ May be respectively the same as described herein.

In embodiments, R in formula 5-1 ₁₁ May be a group represented by formula 1-1.

In embodiments, the fifth compound may be compound 5-1:

compound 5-1-

A light emitting device according to an embodiment of the present disclosure has an inverted structure in which a substrate, a cathode, an organic layer composed of an electron transport region, an emission layer, and a hole transport region, and an anode are sequentially formed, wherein the hole transport region includes: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof.

When the hole transport region includes the first compound, the second compound, the fifth compound, or any combination thereof, low-temperature thermal curing or low-temperature photo-curing may occur, thereby minimizing thermal decomposition of the emission layer that may occur during high-temperature thermal curing.

In addition, the light emitting device having such an inverted structure may include: an electron transport region including a third compound which is a metal oxide; and a hole transport region including the first compound, the second compound, the fifth compound, or any combination thereof, thereby exhibiting excellent efficiency characteristics and long life characteristics.

The hole transport region may include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof:

formula 201

Formula 202

In the case of the equations 201 and 202,

L ₂₀₁ to L ₂₀₄ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

L ₂₀₅ can be selected from-O-, -S-, -N (Q) ₂₀₁ ) -, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₂₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₂₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

xa1 to xa4 may each independently be an integer from 0 to 5,

xa5 may be an integer from 1 to 10,

R ₂₀₁ to R ₂₀₄ And Q ₂₀₁ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

R ₂₀₁ and R ₂₀₂ Optionally bonded to each other by: singly bound, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₅ Alkylene, or unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₅ Alkenylene to form unsubstituted or substituted by at least one R _10a Substituted C ₈ -C ₆₀ Polycyclic groups (e.g., carbazolyl or the like) (e.g., compound HT 16),

R ₂₀₃ and R ₂₀₄ Optionally bonded to each other by: is singly bound, unsubstituted or substituted byAt least one R _10a Substituted C ₁ -C ₅ Alkylene, or unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₅ Alkenylene to form unsubstituted or substituted by at least one R _10a Substituted C ₈ -C ₆₀ A polycyclic radical, and

na1 may be an integer from 1 to 4.

For example, each of formulas 201 and 202 may include at least one of the groups represented by formulas CY201 through CY 217:

in formulae CY201 to CY217, R _10b And R _10c Can each be related to R _10a As described, ring CY ₂₀₁ To ring CY ₂₀₄ May each independently be C ₃ -C ₂₀ Carbocyclic group or C ₁ -C ₂₀ A heterocyclic group, and at least one hydrogen in formulae CY201 through CY217 may be unsubstituted or substituted with R as described above _10a And (4) substitution.

In embodiments, ring CY in formulas CY201 through CY217 ₂₀₁ To ring CY ₂₀₄ May each independently be phenyl, naphthyl, phenanthryl or anthracyl.

In one or more embodiments, each of formula 201 and formula 202 may include at least one of the groups represented by formula CY201 through formula CY 203.

In one or more embodiments, formula 201 can include at least one of the groups represented by formulae CY201 through CY203 and at least one of the groups represented by formulae CY204 through CY 217.

In one or more embodiments, in formula 201, xa1 can be 1,R ₂₀₁ May be a group represented by one of formulae CY201 to CY203, xa2 may be 0, and R ₂₀₂ May be a group represented by one of formulae CY204 to CY 207.

In one or more embodiments, each of formula 201 and formula 202 may not include groups represented by formula CY201 through formula CY 203.

In one or more embodiments, each of formula 201 and formula 202 may not include groups represented by formula CY201 through formula CY203, and may include at least one of the groups represented by formula CY204 through formula CY 217.

In one or more embodiments, each of formula 201 and formula 202 may not include groups represented by formula CY201 through formula CY 217.

For example, the hole transport region may comprise one of: compounds HT1 through compounds HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β -NPB, TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), or any combination thereof:

/>

/>

/>

/>

the hole transport region may have a thickness of about

To about->

(e.g., about->

To about>

) Within the range of (1). When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the hole injection layer can have a thickness that is about { [ MEANS ] } greater than or equal to>

To about->

(e.g., about +>

To about->

) And the thickness of the hole transport layer may be about

To about->

(e.g., about->

To about->

) Within the range of (1). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.

The emission auxiliary layer may improve light emission efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the emission layer, and the electron blocking layer may block leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission assisting layer and the electron blocking layer.

[ P-dopant ]

In addition to these materials, the hole transport region may further include a charge generation material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer composed of the charge generating material).

The charge generating material can be, for example, a p-dopant.

For example, the Lowest Unoccupied Molecular Orbital (LUMO) energy level of the p-dopant can be about-3.5 eV or less.

In embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, a compound including the element EL1 and the element EL2, or any combination thereof.

Examples of quinone derivatives are TCNQ, F4-TCNQ, and the like.

Examples of the cyano group-containing compound are HAT-CN, a compound represented by formula 221, and the like:

formula 221

In formula 221, R ₂₂₁ To R ₂₂₃ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group, and

R ₂₂₁ to R ₂₂₃ May each independently be C ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ Heterocyclic radicalEach of which is substituted by: a cyano group; -F; -Cl; -Br; -I; c substituted by cyano, -F, -Cl, -Br, -I or any combination thereof ₁ -C ₂₀ An alkyl group; or any combination thereof.

In the compound including the element EL1 and the element EL2, the element EL1 may be a metal, a metalloid, or any combination thereof, and the element EL2 may be a nonmetal, a metalloid, or any combination thereof.

Examples of metals are: alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and the like); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and the like); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), and the like); late transition metals (e.g., zinc (Zn), indium (In), tin (Sn), and the like); lanthanide metals (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and the like); and the like.

Examples of metalloids are silicon (Si), antimony (Sb), tellurium (Te) and the like.

Examples of the nonmetal include oxygen (O), halogen (e.g., F, cl, br, I, and the like), and the like.

Examples of the compound including the element EL1 and the element EL2 are metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides, metal iodides, and the like), metalloid halides (e.g., metalloid fluorides, metalloid chlorides, metalloid bromides, metalloid iodides, and the like), metal tellurides, or any combination thereof.

Illustrative of the metal oxide are tungsten oxides (e.g., WO, W) ₂ O ₃ 、WO ₂ 、WO ₃ 、W ₂ O ₅ And the like), vanadium oxide (e.g., VO, V) ₂ O ₃ 、VO ₂ 、V ₂ O ₅ And the like), molybdenum oxide (MoO, mo) ₂ O ₃ 、MoO ₂ 、MoO ₃ 、Mo ₂ O ₅ And the like), rhenium oxide (e.g., reO) ₃ And the like) and the like.

Examples of metal halides are alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, lanthanide metal halides, and the like.

Examples of alkali metal halides are LiF, naF, KF, rbF, csF, liCl, naCl, KCl, rbCl, csCl, liBr, naBr, KBr, rbBr, csBr, liI, naI, KI, rbI, csI, and the like.

Examples of alkaline earth halides are BeF ₂ 、MgF ₂ 、CaF ₂ 、SrF ₂ 、BaF ₂ 、BeCl ₂ 、MgCl ₂ 、CaCl ₂ 、SrCl ₂ 、BaCl ₂ 、BeBr ₂ 、MgBr ₂ 、CaBr ₂ 、SrBr ₂ 、BaBr ₂ 、BeI ₂ 、MgI ₂ 、CaI ₂ 、SrI ₂ 、BaI ₂ And the like.

Examples of transition metal halides are: titanium halides (e.g. TiF) ₄ 、TiCl ₄ 、TiBr ₄ 、TiI ₄ And the like), zirconium halides (e.g., zrF ₄ 、ZrCl ₄ 、ZrBr ₄ 、ZrI ₄ And the like), hafnium halides (e.g., hfF) ₄ 、HfCl ₄ 、HfBr ₄ 、HfI ₄ And the like), vanadium halides (e.g., VF) ₃ 、VCl ₃ 、VBr ₃ 、VI ₃ And the like), niobium halides (e.g., nbF ₃ 、NbCl ₃ 、NbBr ₃ 、NbI ₃ And the like), tantalum halides (e.g., taF) ₃ 、TaCl ₃ 、TaBr ₃ 、TaI ₃ And the like), chromium halides (e.g., crF) ₃ 、CrCl ₃ 、CrBr ₃ 、CrI ₃ And the like), molybdenum halides (e.g., moF) ₃ 、MoCl ₃ 、MoBr ₃ 、MoI ₃ And the like), tungsten halides (e.g., WF) ₃ 、WCl ₃ 、WBr ₃ 、WI ₃ And the like), manganese halides (e.g., mnF) ₂ 、MnCl ₂ 、MnBr ₂ 、MnI ₂ And the like), technetium halides (e.g., tcF) ₂ 、TcCl ₂ 、TcBr ₂ 、TcI ₂ And the like), rhenium halides (e.g., reF) ₂ 、ReCl ₂ 、ReBr ₂ 、ReI ₂ And the like), iron halides (e.g., feF) ₂ 、FeCl ₂ 、FeBr ₂ 、FeI ₂ And the like), ruthenium halides (e.g., ruF) ₂ 、RuCl ₂ 、RuBr ₂ 、RuI ₂ And the like), osmium halides (e.g., osF) ₂ 、OsCl ₂ 、OsBr ₂ 、OsI ₂ And the like), cobalt halides (e.g., coF) ₂ 、CoCl ₂ 、CoBr ₂ 、CoI ₂ And the like), rhodium halides (e.g., rhF) ₂ 、RhCl ₂ 、RhBr ₂ 、RhI ₂ And the like), iridium halides (e.g., irF) ₂ 、IrCl ₂ 、IrBr ₂ 、IrI ₂ And the like), nickel halides (e.g., niF) ₂ 、NiCl ₂ 、NiBr ₂ 、NiI ₂ And the like), palladium halides (e.g., pdF) ₂ 、PdCl ₂ 、PdBr ₂ 、PdI ₂ And the like), platinum halides (e.g., ptF) ₂ 、PtCl ₂ 、PtBr ₂ 、PtI ₂ And the like), copper halides (e.g., cuF, cuCl, cuBr, cuI, and the like), silver halides (e.g., agF, agCl, agBr, agI, and the like), gold halides (e.g., auF, auCl, auBr, auI, and the like), and the like.

Examples of late transition metal halides are zinc halides (e.g., znF) ₂ 、ZnCl ₂ 、ZnBr ₂ 、ZnI ₂ And the like), indium halides (e.g., inI) ₃ And the like), tin halides (e.g., snI) ₂ And the like) and the like.

Examples of lanthanide metal halides are YbF, ybF ₂ 、YbF ₃ 、SmF ₃ 、YbCl、YbCl ₂ 、YbCl ₃ 、SmCl ₃ 、YbBr、YbBr ₂ 、YbBr ₃ 、SmBr ₃ 、YbI、YbI ₂ 、YbI ₃ 、SmI ₃ And the like.

An example of a metalloid halide is antimony halide (e.g., sbCl) ₅ And the like) and the like.

Examples of the metal telluride are alkali metal tellurides (e.g., li) ₂ Te、Na ₂ Te、K ₂ Te、Rb ₂ Te、Cs ₂ Te and the like), alkaline earth metal tellurides (e.g., beTe, mgTe, caTe, srTe, baTe and the like), transition metal tellurides (e.g., tiTe ₂ 、ZrTe ₂ 、HfTe ₂ 、V ₂ Te ₃ 、Nb ₂ Te ₃ 、Ta ₂ Te ₃ 、Cr ₂ Te ₃ 、Mo ₂ Te ₃ 、W ₂ Te ₃ 、MnTe、TcTe、ReTe、FeTe、RuTe、OsTe、CoTe、RhTe、IrTe、NiTe、PdTe、PtTe、Cu ₂ Te、CuTe、Ag ₂ Te、AgTe、Au ₂ Te and the like), laTe transition metal tellurides (e.g., znTe and the like), lanthanide metal tellurides (e.g., laTe, ceTe, prTe, ndTe, pmTe, euTe, gdTe, tbTe, dyTe, hoTe, erTe, tmTe, ybTe, luTe, and the like), and the like.

[ Anode 150]

An anode 150 is disposed on the hole transport region 140.

The anode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The anode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The anode 150 may have a single layer structure or a multi-layer structure including a plurality of layers.

[ covering layer ]

The first cover layer may be disposed outside the cathode 110, and/or the second cover layer may be disposed outside the anode 150. In detail, the light emitting device 10 may have: a structure in which the first capping layer, the cathode 110, the emission layer 130, and the anode 150 are sequentially stacked in the stated order; a structure in which a cathode 110, an emission layer 130, an anode 150, and a second capping layer are sequentially stacked in the stated order; or a structure in which the first capping layer, the cathode 110, the emission layer 130, the anode 150, and the second capping layer are sequentially stacked in the stated order.

In an embodiment, light generated in the emission layer 130 of the organic layer 160 of the light emitting device 10 may be emitted outward through the cathode 110 and the first capping layer, which are semi-transmissive or transmissive electrodes. In one or more embodiments, light generated in the emission layer 130 of the organic layer 160 of the light emitting device 10 may be emitted outward through the anode 150 and the second capping layer, which are semi-transmissive or transmissive electrodes.

The first cover layer and the second cover layer can improve external emission efficiency according to the principle of constructive interference. Therefore, the light extraction efficiency of the light-emitting device 10 can be improved, so that the light emission efficiency of the light-emitting device 10 can also be improved.

Each of the first cladding layer and the second cladding layer may include a material having a refractive index (at 589 nm) of 1.6 or more.

The first capping layer and the second capping layer may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or an organic-inorganic composite capping layer including an organic material and an inorganic material.

In embodiments, at least one of the first and second cover layers may each independently include a carbocyclic compound, a heterocyclic compound, a compound containing an amine group, a porphyrin derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and compound containing an amine group can each be optionally substituted with substituents comprising O, N, S, se, si, F, cl, br, I, or any combination thereof. In one or more embodiments, at least one of the first and second capping layers may each independently comprise a compound comprising an amine group.

In one or more embodiments, at least one of the first cover layer and the second cover layer may each independently comprise a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.

In one or more embodiments, at least one of the first cover layer and the second cover layer may each independently comprise: one of compound HT28 to compound HT33, one of compound CP1 to compound CP6, β -NPB, or any combination thereof:

[ electronic apparatus ]

The light emitting device may be included in various electronic apparatuses. For example, the electronic device including the light-emitting apparatus may be a light-emitting device, an authentication device, or the like.

In addition to the light emitting device, the electronic apparatus (e.g., light emitting apparatus) may further include i) a color filter, ii) a color conversion layer, or iii) both a color filter and a color conversion layer. The color filter and/or the color conversion layer may be arranged in at least one propagation direction of light emitted from the light emitting device. For example, the light emitted from the light emitting device may be blue light or white light. The details of the light emitting device may be the same as described herein. In an embodiment, the color conversion layer may include quantum dots. The quantum dots can be, for example, the same as described herein.

An electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, the color filter may include a plurality of color filter regions respectively corresponding to the plurality of sub-pixel regions, and the color conversion layer may include a plurality of color conversion regions respectively corresponding to the plurality of sub-pixel regions.

The pixel defining film may be disposed among the plurality of sub-pixel regions to define each of the sub-pixel regions.

The color filter may further include a plurality of color filter regions and light-shielding patterns disposed among the color filter regions, and the color conversion layer may further include a plurality of color conversion regions and light-shielding patterns disposed among the color conversion regions.

The plurality of color filter regions (or the plurality of color conversion regions) may include: a first region emitting a first color light; a second region emitting a second color light; and/or a third region emitting a third color light, wherein the first, second, and/or third color lights may have different maximum emission wavelengths from each other. For example, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. For example, the plurality of color filter regions (or the plurality of color conversion regions) may include quantum dots. In particular, the first region may include red quantum dots, the second region may include green quantum dots, and the third region may not include quantum dots. The details of the quantum dots can be the same as described herein. The first region, the second region and/or the third region may each further comprise a scatterer.

For example, the light emitting device can emit a first light, the first region can absorb the first light and emit a1 st-1 st color light, the second region can absorb the first light and emit a2 nd-1 st color light, and the third region can absorb the first light and emit a 3 rd-1 st color light. Here, the 1 st-1 st color light, the 2 nd-1 st color light, and the 3 rd-1 st color light may have maximum emission wavelengths different from each other. Specifically, the first light may be blue light, the 1 st-1 st color light may be red light, the 2 nd-1 st color light may be green light, and the 3 rd-1 st color light may be blue light.

In addition to the above light-emitting device, the electronic apparatus may further include a thin film transistor. The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of a first electrode and a second electrode of the light emitting device.

The thin film transistor may further include a gate electrode, a gate insulating film, or the like.

The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, or the like.

The electronic apparatus may further include a sealing portion for sealing the light emitting device. The sealing portion may be disposed between the color conversion layer and/or the color filter and the light emitting device. The sealing portion allows light to pass from the light emitting device to the outside, and simultaneously prevents air and moisture from penetrating into the light emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate or a plastic substrate. The sealing portion may be a thin film encapsulation layer including at least one of an organic layer and/or an inorganic layer. When the sealing portion is a thin film encapsulation layer, the electronic device may be flexible.

In addition to the color filter and/or the color conversion layer, various functional layers may be disposed on the sealing part according to the use of the electronic device. The functional layers may include touch screen layers, polarizing layers, and the like. The touch screen layer can be a pressure-sensitive touch screen layer, a capacitive touch screen layer or an infrared touch screen layer.

The authentication apparatus may further include a biological information collector in addition to the light emitting device as described above. The authentication device may be, for example, a biometric authentication device that authenticates an individual by using biometric information of a living body (e.g., fingertips, pupils, and the like).

The electronic device can be applied to various displays, light sources, lighting, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notepads, electronic dictionaries, electronic game machines, medical instruments (e.g., electronic thermometers, blood pressure meters, blood glucose meters, pulse wave meters, electrocardiogram displays, ultrasonic diagnostic machines, or endoscope displays), fish finders, various measuring instruments, meters (e.g., meters for vehicles, airplanes, and ships), projectors, and the like.

[ description of FIG. 2]

Another aspect of the present disclosure provides a light emitting device including:

a substrate;

a cathode disposed on the substrate;

an anode facing the cathode;

x light-emitting units between the cathode and the anode; and

x-1 charge generation layers each disposed between two adjacent light emitting cells among the x light emitting cells and including an n-type charge generation layer and a p-type charge generation layer,

wherein, x may be an integer of 2 or more,

each of the x light emitting units may include an electron transport region, an emission layer, and a hole transport region sequentially arranged from the cathode, and

the hole transport region may include: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof.

The first compound, the second compound, and the fifth compound may be the same as described herein.

Fig. 2 is a schematic cross-sectional view of a light emitting device 20 according to another embodiment. As shown in fig. 2, the light emitting device 20 includes a substrate 100, a cathode 110 on the substrate 100, an anode 150 facing the cathode 100, 2

light emitting units

10A and 10B stacked between the cathode 100 and the

anode

150, and 1 charge generation layer 145, the charge generation layer 145 including an n-type charge generation layer and a p-type charge generation layer.

The

light emitting units

10A and 10B may include

electron transport regions

120A and 120B,

emission layers

130A and 130B, and

hole transport regions

140A and 140B, respectively, sequentially stacked in the stated order from the cathode 100.

The "light emitting device" may include x light emitting units, wherein x may be an integer of 2 or more. The number x of the light emitting units may vary according to purposes, and the upper limit of the number is not particularly limited. For example, the light emitting device may include 2,3,4, 5, or 6 light emitting cells.

The light emitting device may include a charge generation layer between two adjacent light emitting cells of the x light emitting cells. Herein, the term "adjacent" refers to an arrangement relationship of layers or units closest to each other from among layers or units referred to as adjacent. For example, "two adjacent light emitting units" refers to an arrangement relationship of two light emitting units arranged closest to each other among the plurality of light emitting units. The term "adjacent" may refer to a situation where two layers or units are in physical contact with each other and a situation where another layer or unit, not mentioned, may be disposed between the two layers or units. For example, the light emitting unit adjacent to the anode refers to a light emitting unit disposed closest to the anode among the plurality of light emitting units. In addition, the anode and the light emitting cell adjacent thereto may be in physical contact with each other. However, in the embodiment, other layers or units than the light emitting unit may be disposed between the anode and the light emitting unit adjacent thereto. In an embodiment, the electron transport layer may be disposed between the anode and the light emitting unit adjacent thereto. However, the charge generation layer may be disposed between two adjacent light emitting cells.

The "charge generation layer" may generate electrons with respect to one of two adjacent light emitting units and thus serve as a cathode, and may generate holes with respect to the other light emitting unit and thus serve as an anode. The charge generation layer is not directly connected to the electrodes, and may separate adjacent light emitting cells. That is, a light emitting device including x light emitting cells may include x-1 charge generation layers.

In an embodiment, the charge generation layer 145 may include a hole transport material.

In one or more embodiments, the charge generation layer 145 can include PEDOT: PSS, nafion, sulfonic acids, and the like.

In one or more embodiments, the charge generation layer 145 may include a fourth compound represented by formula 4:

formula 4

In the formula 4, the first and second organic solvents are,

e can be B, al, ga, in or Tl,

R ₄₁ to R ₄₄ May each independently be unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic radicals being either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group, and

R _10a may be the same as described herein.

In embodiments, E in formula 4 may be B.

In embodiments, R ₄₁ To R ₄₄ May each independently be unsubstituted or substituted with at least one R _10a Substituted C ₁ -C ₁₀ Heterocycloalkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Arylene, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heteroarylene, unsubstituted or substituted by at least one R _10a A substituted monovalent non-aromatic fused polycyclic group, either unsubstituted or substituted with at least one R _10a A substituted monovalent non-aromatic fused heteropolycyclic group.

In one or more embodiments, R ₄₁ To R ₄₄ Can be respectively and independently at least one of-F and C ₂ -C ₁₀ Alkenyl radical, C ₆ -C ₆₀ Arylene or monovalent non-aromatic fused polycyclic group substituted phenyl.

In embodiments, the fourth compound may be one of compound 4-1 to compound 4-6:

compound 4-1

Compound 4-2

Compound 4-3

Compound 4-4

Compounds 4 to 5

Compounds 4 to 6

In the light-emitting device including x light-emitting units according to an embodiment of the present disclosure, each of the x light-emitting units includes an electron transporting region including a third compound which is a metal oxide and a hole transporting region including the first compound or the second compound so as to exhibit excellent efficiency characteristics and long life characteristics.

Each of the x-1 charge generation layers may include an n-type charge generation layer and a p-type charge generation layer. Here, the n-type charge generation layer and the p-type charge generation layer may directly contact each other to form an NP junction. By the NP junction, electrons and holes can be simultaneously generated between the n-type charge generation layer and the p-type charge generation layer. The generated electrons may be transferred to one of two adjacent light emitting cells through the n-type charge generation layer. The generated holes may move to the other of the two adjacent light emitting cells through the p-type charge generation layer. Further, in the case where there are a plurality of charge generation layers, each of the plurality of charge generation layers includes one n-type charge generation layer and one p-type charge generation layer. That is, the light emitting device including x-1 charge generation layers may include x-1 n-type charge generation layers and x-1 p-type charge generation layers.

n-type refers to n-type semiconductor characteristics, i.e., the characteristics of injecting or transporting electrons. p-type refers to p-type semiconductor characteristics, i.e., the characteristics of injecting or transporting holes.

The x light emitting cells may respectively include an electron transport region, an emission layer, and a hole transport region sequentially arranged in this stated order from the cathode 110. Here, each of the x electron transport regions included in the x light emitting units may include a third compound represented by formula 3, and each of the x hole transport regions included in the x light emitting units may include a first compound including a first repeating unit represented by formula 1 and a second compound represented by formula 2.

Each of the plurality of hole transport regions may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and each of the plurality of electron transport regions may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In embodiments, the maximum emission wavelengths of light emitted from the x light-emitting units may all be the same.

In one or more embodiments, x light-emitting units may emit blue light having a maximum emission wavelength of about 420nm or more and about 490nm or less.

In one or more embodiments, x light-emitting units may emit red light having a maximum emission wavelength of about 620nm or more and about 750nm or less.

In one or more embodiments, the x light emitting units may emit green light having a maximum emission wavelength of about 495nm or more and about 580nm or less.

In one or more embodiments, the maximum emission wavelength of light emitted from at least one of the x light-emitting units may be different from the maximum emission wavelength of light emitted from at least one of the remaining light-emitting units. For example, in the case of a light emitting device in which a first light emitting unit and a second light emitting unit are stacked, the maximum emission wavelength of light emitted from the first light emitting unit may be different from the maximum emission wavelength of light emitted from the second light emitting unit. In this case, the emission layer of the first light emitting unit and the emission layer of the second light emitting unit may each independently have: i) A single layer structure composed of a single layer composed of a single material; ii) a single layer structure consisting of a single layer, the single layer consisting of a plurality of different materials; or iii) a multilayer structure having a plurality of layers, the plurality of layers being composed of different materials. Accordingly, the light emitted from the first light emitting unit or the light emitted from the second light emitting unit may be monochromatic light or mixed color light. For example, in the case of a light emitting device in which a first light emitting unit, a second light emitting unit, and a third light emitting unit are stacked, the maximum emission wavelength of light emitted from the first light emitting unit may be the same as the maximum emission wavelength of light emitted from the second light emitting unit, but may be different from the maximum emission wavelength of light emitted from the third light emitting unit. Alternatively, the maximum emission wavelength of light emitted from the first light-emitting unit, the maximum emission wavelength of light emitted from the second light-emitting unit, and the maximum emission wavelength of light emitted from the third light-emitting unit may be different from each other.

[ production method ]

The emission layer and the constituent layers of the electron transport region and the hole transport region may be formed using a solution method.

Another aspect of the present disclosure provides a method of manufacturing a light emitting device, the method including: forming a first organic layer between the cathode and the anode; forming a second organic layer between the anode and the first organic layer; and forming a third organic layer between the second organic layer and the anode.

In embodiments, the first organic layer may be a hole transport region, the second organic layer may be an emissive layer, and the third organic layer may be an electron transport region.

In one or more embodiments, a separate organic layer may be formed between the first organic layer and the second organic layer, and a separate organic layer may be formed between the second organic layer and the third organic layer.

In embodiments, the formation of the first organic layer may be performed by a solution method using a composition including the third compound represented by formula 3.

The third compound can be the same as described herein.

The amount of the third compound included in the composition may be about 1wt% or more and about 5wt% or less, or about 2wt% or more and about 4wt% or less, based on the total amount of the composition of 100 wt%.

In embodiments, the formation of the second organic layer may be performed by a solution process using a composition including a host compound, a dopant compound, a delayed fluorescence material, a quantum dot, or any combination thereof.

The host compound, dopant compound, delayed fluorescence material, and quantum dot may each be the same as described herein.

When the composition includes only the host compound, the amount of the host compound included in the composition may be about 1wt% or more and about 5wt% or less, or about 2wt% or more and about 4wt% or less, based on 100wt% of the total amount of the composition.

When the composition includes both the host compound and the dopant compound, the amount of the dopant compound included in the composition may be about 1wt% or more and about 5wt% or less, or about 2wt% or more and about 4wt% or less, based on 100wt% of the total amount of the host compound.

When the composition includes only the quantum dots, the amount of the quantum dots included in the composition may be about 0.1wt% or more and about 3wt% or less, or about 0.5wt% or more and about 2wt% or less, based on 100wt% of the total amount of the composition.

In embodiments, the formation of the third organic layer may be performed by a solution method using a composition including a first compound including a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof.

The first compound, the second compound, and the fifth compound can each be the same as described herein.

When the composition includes only the first compound or only the fifth compound, the amount of the first compound or the fifth compound may be about 0.5wt% or more and about 4wt% or less, or about 1.5wt% or more and about 3wt% or less, based on 100wt% of the total amount of the composition.

When the composition includes both the first compound and the second compound, the amount of the second compound included in the composition may be about 2wt% or more and about 10wt% or less, or about 3wt% or more and about 7wt% or less, based on 100wt% of the first compound.

In embodiments, the method may further include forming a fourth organic layer between the third organic layer and the anode.

In embodiments, the formation of the fourth organic layer may be performed by a solution method using a composition including a hole transport material, a fourth compound represented by formula 4, or any combination thereof.

The hole transport material and the fourth compound may each be the same as described herein.

For example, the hole transport material may be PEDOT: PSS, nafion or sulfonic acid.

The solution process may be performed by spin coating, slot coating, dip coating, bar coating, roll coating, gravure coating, micro gravure coating, wire coating, spray coating, ink jet printing, nozzle printing, screen printing, flexo printing, offset printing, or casting.

For example, the solution method may be performed by spin coating.

In an embodiment, each of the formation of the first organic layer, the formation of the second organic layer, and the formation of the third organic layer may further include a step of evaporating the solvent.

In one or more embodiments, the forming of the fourth organic layer may further include a step of evaporating the solvent.

The evaporation of the solvent may be carried out at a temperature in the range of about 110 ℃ to about 180 ℃.

In one or more embodiments, the method can further comprise: a step of irradiating UV before the evaporation of the solvent.

In an embodiment, the forming of the first organic layer may include: coating (e.g., spin coating) a composition comprising a third compound; irradiating the coated composition with ultraviolet rays; the solvent was evaporated after uv irradiation.

In an embodiment, the forming of the second organic layer may include: coating (e.g., spin coating) a composition comprising a host compound, a dopant compound, a delayed fluorescence material, a quantum dot, or any combination thereof; irradiating the coated composition with ultraviolet rays; and evaporating the solvent after the ultraviolet irradiation.

In embodiments, the forming of the third organic layer may include: coating (e.g., spin coating) a composition comprising a first compound, a second compound, or any combination thereof; irradiating the coated composition with ultraviolet rays; and evaporating the solvent after the ultraviolet irradiation.

In an embodiment, a light emitting device including x light emitting cells may be manufactured by performing the following steps: the first organic layer, the second organic layer, and the third organic layer are formed in the stated order. Next, a step of forming a fourth organic layer may be performed. Thereafter, a light-emitting device can be manufactured by repeating the same steps as forming the first organic layer, forming the second organic layer, and forming the third organic layer in the stated order.

In an embodiment, a light emitting device including x light emitting cells may be manufactured by performing the following steps: the first organic layer, the second organic layer, and the third organic layer are formed in the stated order. Next, a step of forming a fourth organic layer may be performed. After that, a light-emitting device can be manufactured by repeating the same steps as forming the first organic layer, forming the second organic layer, and forming the third organic layer in the stated order, except that a composition having a different composition from each of the compositions for forming the first to third organic layers is used.

[ description of FIGS. 3 and 4 ]

Fig. 3 is a cross-sectional view showing a light emitting apparatus according to an embodiment.

The light emitting apparatus of fig. 3 includes a substrate 100, a Thin Film Transistor (TFT), a light emitting device, and a package portion 300 sealing the light emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. The buffer layer 210 may be disposed on the substrate 100. The buffer layer 210 may prevent impurities from penetrating the substrate 100 and may provide a flat surface on the substrate 100.

The TFT may be disposed on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The active layer 220 may include an inorganic semiconductor such as silicon or polysilicon, an organic semiconductor, or an oxide semiconductor, and may include a source region, a drain region, and a channel region.

A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be disposed on the active layer 220, and the gate electrode 240 may be disposed on the gate insulating film 230.

An interlayer insulating film 250 may be disposed on the gate electrode 240. An interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 so as to be insulated from each other.

The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose source and drain regions of the active layer 220, and the source and drain

electrodes

260 and 270 may be disposed to contact the exposed portions of the source and drain regions of the active layer 220.

The TFT may be electrically connected to a light emitting device to drive the light emitting device, and may be protected to be covered with the passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light emitting device may be provided on the passivation layer 280. The light emitting device includes a first electrode 110, an emission layer 130, and a second electrode 150.

The first electrode 110 may be disposed on the passivation layer 280. The passivation layer 280 may be disposed to expose a portion of the drain electrode 270, not to completely cover the drain electrode 270, and the first electrode 110 may be disposed to be connected to the exposed portion of the drain electrode 270.

A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining film 290 may expose a region of the first electrode 110, and the emission layer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide-based organic film or a polyacrylic-based organic film. At least some of the emission layers 130 may extend beyond an upper portion of the pixel defining layer 290 to be arranged in the form of a common layer.

The second electrode 150 may be disposed on the emission layer 130, and the capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

The encapsulation portion 300 may be disposed on the cover layer 170. The encapsulation portion 300 may be disposed on the light emitting device to protect the light emitting device from moisture or oxygen. The encapsulation part 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyvinyl sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate, polyacrylic acid, and the like), epoxy-based resins (e.g., aliphatic Glycidyl Ether (AGE), and the like), or any combination thereof; or any combination of inorganic and organic films.

Fig. 4 is a cross-sectional view of a light emitting apparatus according to another embodiment.

The light emitting device of fig. 4 is the same as the light emitting device of fig. 3 except that the light blocking pattern 500 and the functional region 400 are additionally arranged on the encapsulation portion 300. The functional region 400 may be i) a color filter region, ii) a color conversion region, or iii) a combination of a color filter region and a color conversion region. In an embodiment, the light emitting devices included in the light emitting apparatus of fig. 3 may be tandem light emitting devices.

[ definition of terms ]

The term "C" as used herein ₃ -C ₆₀ The carbocyclic group "means a cyclic group consisting of only carbon as a ring-forming atom and having 3 to 60 carbon atoms, and the term" C "as used herein ₁ -C ₆₀ The heterocyclic group "means a cyclic group having 1 to 60 carbon atoms and additionally having a hetero atom as a ring-constituting atom in addition to carbon. C ₃ -C ₆₀ Carbocyclic group and C ₁ -C ₆₀ The heterocyclic groups may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are fused to each other. E.g. C ₁ -C ₆₀ The heterocyclic group has 3 to 61 ring-constituting atoms.

As used herein, "cyclic group" may include C ₃ -C ₆₀ Carbocyclic group and C ₁ -C ₆₀ A heterocyclic group.

The term "pi electron rich C" as used herein ₃ -C ₆₀ Cyclic group "refers to a cyclic group having 3 to 60 carbon atoms and not including-N =' as a ring forming moiety, and the term" nitrogen containing C lacking pi electrons as used herein ₁ -C ₆₀ The cyclic group "means a heterocyclic group having 1 to 60 carbon atoms and including = as a ring-forming moiety.

E.g. C ₃ -C ₆₀ The carbocyclic group may be: i) T1 group or ii) a condensed cyclic group in which two or more T1 groups are condensed with each other (for example, cyclopentadienyl group, adamantyl group, norbornyl group, phenyl group, pentalenyl group, naphthyl group,Azulenyl, indacenaphthenyl, phenacenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,

A group selected from the group consisting of a phenyl group, a perylene group, a pentacenyl group, a heptenylene group, a tetracenyl group, a picene group, a hexacophenyl group, a pentacenyl group, a rubicene group, a hexacophenyl group, an egg phenyl group, an indenyl group, a fluorenyl group, a spiro-bisfluorenyl group, a benzofluorenyl group, an indenophenanthryl group or an indenonanthryl group),

C ₁ -C ₆₀ the heterocyclic group may be: i) A T2 group, ii) a fused cyclic group in which two or more T2 groups are fused to each other, <xnotran> iii) T2 T1 (, , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , . </xnotran>Dibenzothienyl, azadibenzofuran groups, and the like),

c rich in pi electrons ₃ -C ₆₀ The cyclic group may be: i) A T1 group, ii) a fused cyclic group in which two or more T1 groups are fused to each other, iii) a T3 group, iv) a fused cyclic group in which two or more T3 groups are fused to each other, or v) a fused cyclic group in which at least one T3 group and at least one T1 group are fused to each other (for example, C ₃ -C ₆₀ Carbocyclic groups, 1H-pyrrolyl, silacyclopentadienyl (silole), boroheterocyclopentadienyl (borole), 2H-pyrrolyl, 3H-pyrrolyl, thienyl, furyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzindolyl, naphthoisoindolyl, benzoxoheterocyclosilylcyclopentadienyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilacyclopentadienyl, dibenzothienyl, dibenzofuranyl, indenocarbazolyl, indonocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilacarbazolyl, benzindonocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, benzonaphthosilathienyl, benzonaphthosilacyclopentadienyl, benzofurodibenzofuranyl, benzofurodibenzothienyl, benzothiophenyl, benzothienodibenzothienyl, and the like),

nitrogen containing C lacking pi electrons ₁ -C ₆₀ The cyclic group may be: i) A T4 group, ii) a fused cyclic group in which two or more T4 groups are fused to each other, iii) a fused cyclic group in which at least one T4 group and at least one T1 group are fused to each other, iv) a fused cyclic group in which at least one T4 group and at least one T3 group are fused to each other, or v) a fused cyclic group in which at least one T4 group, at least one T1 group and at least one T3 group are fused to each other (for example, pyrazolyl group, imidazolyl group, triazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzopyrazolyl group, benzimidazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, benzisothiazolyl group, pyridyl group, pyrimidyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolyl group, benzoquinolyl groupIsoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cinnolinyl, phthalazinyl, naphthyridinyl, imidazopyridine, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzosilacyclopentadienyl, azadibenzothienyl, azadibenzofuran groups, and the like),

the T1 group may be a cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornane (or bicyclo [2.2.1] heptane) group, norbornenyl, bicyclo [1.1.1] pentane, bicyclo [2.1.1] pentane, bicyclo [2.2.2] octane or phenyl group,

the T2 group may be furyl, thienyl, 1H-pyrrolyl, silacyclopentadienyl, boracyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilacyclopentadienyl, azaboroheterocyclopentadienyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, tetrazinyl, pyrrolidinyl, imidazolidinyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyridazinyl or dihydropyridazinyl,

the T3 group may be furyl, thienyl, 1H-pyrrolyl, siloxycyclopentadienyl or boroheterocyclopentadienyl, and

the T4 group can be 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azasilacyclopentadienyl (azasilole), azaboropentadienyl (azaborole), pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetrazinyl.

The term "cyclic group, C as used herein ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic radical, pi-electron rich C ₃ -C ₆₀ Cyclic group or nitrogen-containing C lacking pi electrons ₁ -C ₆₀ Cyclic group "means a group condensed with any cyclic group, monovalent group, or polyvalent group (e.g., divalent group, trivalent group, tetravalent group, and the like) according to the structure of formula (la) where the corresponding term is used. For example, "phenyl" may be a benzo group, phenyl, phenylene, or the like, which can be readily understood by one of ordinary skill in the art based on the structure of the formula including "phenyl".

Monovalent C ₃ -C ₆₀ Carbocyclic group and monovalent C ₁ -C ₆₀ Examples of heterocyclic groups are C ₃ -C ₁₀ Cycloalkyl radical, C ₁ -C ₁₀ Heterocycloalkyl radical, C ₃ -C ₁₀ Cycloalkenyl radical, C ₁ -C ₁₀ Heterocycloalkenyl, C ₆ -C ₆₀ Aryl radical, C ₁ -C ₆₀ A monovalent non-aromatic fused polycyclic group and a monovalent non-aromatic fused heteropolycyclic group. Divalent C ₃ -C ₆₀ Carbocyclic group and divalent C ₁ -C ₆₀ Examples of heterocyclic radicals are C ₃ -C ₁₀ Cycloalkylene radical, C ₁ -C ₁₀ Heterocycloalkylene, C ₃ -C ₁₀ Cycloalkenylene group, C ₁ -C ₁₀ Heterocyclylene radical, C ₆ -C ₆₀ Arylene radical, C ₁ -C ₆₀ A heteroarylene group, a divalent non-aromatic fused polycyclic group, and a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group.

The term "C" as used herein ₁ -C ₆₀ The alkyl group "means a straight or branched chain aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-pentyl group, 3-pentyl group, sec-pentyl group, isopentyl group, sec-hexyl group, sec-heptyl group, isoheptyl group, sec-heptyl group, and the like,N-decyl, isodecyl, secondary decyl, tertiary decyl, and the like. The term "C" as used herein ₁ -C ₆₀ Alkylene "means having a carbon atom with C ₁ -C ₆₀ Alkyl groups are divalent radicals of the same structure.

The term "C" as used herein ₂ -C ₆₀ Alkenyl "means having at C ₂ -C ₆₀ A monovalent hydrocarbon group of at least one carbon-carbon double bond in the middle or at the end of the alkyl group, and its examples are vinyl, propenyl, butenyl, and the like. The term "C" as used herein ₂ -C ₆₀ Alkenylene "means having an alkyl group with C ₂ -C ₆₀ And divalent groups having the same structure as the alkenyl group.

The term "C" as used herein ₂ -C ₆₀ Alkynyl "means having at C ₂ -C ₆₀ A monovalent hydrocarbon group of at least one carbon-carbon triple bond in the middle or at the end of the alkyl group, and is exemplified by ethynyl, propynyl, and the like. The term "C" as used herein ₂ -C ₆₀ Alkynylene "means having an alkyl group with C ₂ -C ₆₀ Alkynyl is a divalent radical of the same structure.

The term "C" as used herein ₁ -C ₆₀ Alkoxy "means a radical formed from-OA ₁₀₁ A monovalent group of (wherein, A) ₁₀₁ Is C ₁ -C ₆₀ Alkyl), and exemplified by methoxy, ethoxy, isopropoxy, and the like.

The term "C" as used herein ₃ -C ₁₀ Cycloalkyl "refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and is exemplified by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl (or bicyclo [2.2.1] alkyl]Heptyl), bicyclo [1.1.1]Pentyl, bicyclo [2.1.1] s]Hexyl, bicyclo [2.2.1]Octyl and the like. The term "C" as used herein ₃ -C ₁₀ "cycloalkylene" means having an alkyl radical with C ₃ -C ₁₀ A divalent group of the same structure as the cycloalkyl group.

The term "C" as used herein ₁ -C ₁₀ Heterocycloalkyl "means that at least one heteroatom other than carbon atoms is additionally included as a ring formerAnd a monovalent cyclic group having 1 to 10 carbon atoms, and specific examples thereof are 1,2,3, 4-oxatriazolyl, tetrahydrofuryl, tetrahydrothienyl and the like. The term "C" as used herein ₁ -C ₁₀ Heterocycloalkylene "means having a carbon atom with ₁ -C ₁₀ Heterocycloalkyl is a divalent radical of the same structure.

The term "C" as used herein ₃ -C ₁₀ The "cycloalkenyl group" means a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond on its ring, and it has no aromaticity, and specifically exemplified by cyclopentenyl group, cyclohexenyl group, cycloheptenyl group and the like. The term "C" as used herein ₃ -C ₁₀ Cycloalkenyl "means having a group with C ₃ -C ₁₀ A divalent group having the same structure as the cycloalkenyl group.

The term "C" as used herein ₁ -C ₁₀ The heterocycloalkenyl "means a monovalent cyclic group including at least one hetero atom other than carbon atoms as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring structure. C ₁ -C ₁₀ Examples of heterocycloalkenyl are 4, 5-dihydro-1, 2,3, 4-oxatriazolyl, 2, 3-dihydrofuryl, 2, 3-dihydrothienyl, and the like. The term "C" as used herein ₁ -C ₁₀ Heterocycloalkylene "means having a carbon atom with ₁ -C ₁₀ Heterocycloalkyl is a divalent radical of the same structure.

The term "C" as used herein ₆ -C ₆₀ Aryl "refers to a monovalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein the term" C ₆ -C ₆₀ Arylene "refers to a divalent group of a carbocyclic aromatic system having 6 to 60 carbon atoms. C ₆ -C ₆₀ Examples of aryl are phenyl, pentalenyl, naphthyl, azulenyl, indacenyl, acenaphthenyl, phenalenyl, phenanthryl, anthracyl, fluoranthracyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,

Phenyl, perylene, pentaphenyl, heptalenyl, tetracenyl, picene, and pentalenylHexaphenyl, pentacenyl, rubicenyl, coronenyl, egg phenyl and the like. When C is ₆ -C ₆₀ Aryl and C ₆ -C ₆₀ When the arylene groups each include two or more rings, the two or more rings may be fused to each other.

The term "C" as used herein ₁ -C ₆₀ Heteroaryl "refers to a monovalent group having a heterocyclic aromatic system further comprising at least 1 heteroatom other than carbon atoms as a ring-forming atom and from 1 to 60 carbon atoms. The term "C" as used herein ₁ -C ₆₀ Heteroarylene "refers to a divalent group having a heterocyclic aromatic system further comprising at least 1 heteroatom other than carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. C ₁ -C ₆₀ Examples of heteroaryl groups are pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzoquinolinyl, isoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, cinnolinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, and the like. When C is present ₁ -C ₆₀ Heteroaryl and C ₁ -C ₆₀ When the heteroarylenes each comprise two or more rings, the rings may be fused to each other.

The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other (only carbon atoms as ring-forming atoms (for example, having 8 to 60 carbon atoms) and having no aromaticity in its entire molecular structure.

The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group having two or more rings fused to each other, additionally including at least one hetero atom as a ring-forming atom in addition to carbon atoms, and having no aromaticity (e.g., having 1 to 60 carbon atoms) in its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups are: pyrrolyl, thienyl, furanyl, indolyl, benzindolyl, naphthoindolyl, isoindolyl, benzisoindolyl, naphthoisoindolyl, benzosilacyclopentadienyl, benzothienyl, benzofuranyl, carbazolyl, dibenzosilacyclopentadienyl, dibenzothienyl, dibenzofuranyl, azacarbazolyl, azafluorenyl, azadibenzosilacyclopentadienyl, azadibenzothienyl, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzopyrazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indenocarbazolyl, indolocarbazolyl, benzofurocarbazolyl, benzothienocarbazolyl, benzosilacarbazolyl, benzindoindolocarbazolyl, benzonaphthofuranyl, benzonaphthothienyl, naphthobenzothiophenyl, dibenzofuranyl, and dibenzofuranyl analogs. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the above-mentioned monovalent non-aromatic fused heteropolycyclic group.

The term "C" as used herein ₆ -C ₆₀ Aryloxy group "indicates-OA ₁₀₂ (wherein, A) ₁₀₂ Is C ₆ -C ₆₀ Aryl), and the term "C" as used herein ₆ -C ₆₀ Arylthio group "indicating-SA ₁₀₃ (wherein, A) ₁₀₃ Is C ₆ -C ₆₀ Aryl).

The term "C" as used herein ₇ -C ₆₀ Arylalkyl "means-A ₁₀₄ A ₁₀₅ (wherein A) ₁₀₄ Is C ₁ -C ₅₄ Alkylene and A ₁₀₅ Is C ₆ -C ₅₉ Aryl) and the term "C" as used herein ₂ -C ₆₀ Heteroarylalkyl "means-A ₁₀₆ A ₁₀₇ (wherein A is ₁₀₆ Is C ₁ -C ₅₉ Alkylene and A ₁₀₇ Is C ₁ -C ₅₉ Heteroaryl).

The term "R" as used herein _10a "can be:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

C ₁ -C ₆₀ alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl or C ₁ -C ₆₀ Alkoxy, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio group, C ₇ -C ₆₀ Arylalkyl radical, C ₂ -C ₆₀ Heteroarylalkyl, -Si (Q) ₁₁ )(Q ₁₂ )(Q ₁₃ )、-N(Q ₁₁ )(Q ₁₂ )、-B(Q ₁₁ )(Q ₁₂ )、-C(＝O)(Q ₁₁ )、-S(＝O) ₂ (Q ₁₁ )、-P(＝O)(Q ₁₁ )(Q ₁₂ ) Or any combination thereof;

C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio group, C ₇ -C ₆₀ Arylalkyl radical or C ₂ -C ₆₀ Heteroarylalkyl, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₁ -C ₆₀ Alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy radical, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy group, C ₆ -C ₆₀ Arylthio group, C ₇ -C ₆₀ Arylalkyl radical, C ₂ -C ₆₀ Heteroarylalkyl, -Si (Q) ₂₁ )(Q ₂₂ )(Q ₂₃ )、-N(Q ₂₁ )(Q ₂₂ )、-B(Q ₂₁ )(Q ₂₂ )、-C(＝O)(Q ₂₁ )、-S(＝O) ₂ (Q ₂₁ )、-P(＝O)(Q ₂₁ )(Q ₂₂ ) Or any combination thereof; or

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ ) or-P (= O) (Q) ₃₁ )(Q ₃₂ )。

In embodiments described herein, Q ₁ To Q ₃ 、Q ₁₁ To Q ₁₃ 、Q ₂₁ To Q ₂₃ And Q ₃₁ To Q ₃₃ May each independently be: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c ₁ -C ₆₀ An alkyl group; c ₂ -C ₆₀ An alkenyl group; c ₂ -C ₆₀ Alkynyl; c ₁ -C ₆₀ An alkoxy group; c ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ Heterocyclic radicals, each of which is unsubstituted or deuterated, -F, cyano, C ₁ -C ₆₀ Alkyl radical, C ₁ -C ₆₀ Alkoxy, phenyl, biphenyl, or any combination thereof; c ₇ -C ₆₀ An arylalkyl group; or C ₂ -C ₆₀ A heteroarylalkyl group.

The term "heteroatom" as used herein refers to any atom other than a carbon atom. Examples of heteroatoms are O, S, N, P, si, B, ge, se, or any combination thereof.

"Ph" as used herein refers to phenyl, as used herein "Me" refers to methyl, as used herein "Et" refers to ethyl, as used herein "ter-Bu" or "Bu ^t "refers to t-butyl, and" OMe "as used herein refers to methoxy.

"Biphenyl" as used herein refers to a phenyl group substituted with a phenyl group. In other words, "biphenyl" is a compound having C ₆ -C ₆₀ Aryl as a substituent.

The term "terphenyl" as used herein means substituted by biphenylA phenyl group of (2). In other words, "terphenyl" is a substituted phenyl group having a structure substituted by C ₆ -C ₆₀ Aryl substituted C ₆ -C ₆₀ Aryl as a substituent.

Unless otherwise defined, as used herein and refers to binding sites to adjacent atoms in the respective formula or moiety.

Hereinafter, the compound according to the embodiment and the light emitting device according to the embodiment will be described in detail with reference to the following synthetic examples and examples. The phrase "replacing A with B" as used in describing the synthetic examples indicates that an equivalent molar equivalent of B is used in place of A.

Examples

Preparation of ink composition

Ink compositions were prepared in the following configurations shown in table 1.

TABLE 1

Compound A

Compound PTC-U

Preparation examples 1 to 1

A glass substrate (50 mm. Times.50 mm) was spin-coated with HTL-1 to form a film having a thickness of 100nm, and a baking process was performed thereon at 150 ℃ for 10 minutes.

Production examples 1-2 to 1-5 and comparative production examples 1-1 and 1-2

Films were prepared in the same manner as in preparation examples 1-1, respectively, except that the ink compositions shown in Table 3 were used instead of HTL-1, respectively.

Preparation example 2-1

With HTL-3Spin-coating a glass substrate (50 mm. Times.50 mm) to form a film having a thickness of 100nm, and applying UV (80 mJ/cm) having a wavelength of 254nm ² ) The film is irradiated. Then, a baking process was performed thereon at 150 ℃ for 10 minutes.

Preparation examples 2-2 and 2-3 and comparative preparation example 2-1

Films were prepared in the same manner as in preparation examples 1-1, respectively, except that the ink compositions shown in Table 3 were used instead of HTL-3, respectively.

Evaluation example 1

Differences in UV absorbance of the films of the preparation examples 1-1 to 1-5 and 2-1 to 2-3 and the comparative preparation examples 1-1, 1-2 and 2-1 were calculated as described in table 2, and the calculation results are shown in table 3.

TABLE 2

1. UV absorbance measurement of HTL: the HTL film was coated on 100 sheets or more, and UV absorbance spectrum was measured at the center of the single-layer HTL film, where the absorbance of UV abs. λ max was set to 100 (initial state).

2. Dropping a solvent: 50mg of solvent was dropped in the center of a single layer of HTL film using a syringe.

3. Placing: the resulting monolayer HTL single film was placed (30 min) with the solvent droplets in the fume hood not moving or flowing.

4. Removing the solvent: the solvent was removed using a microfiber wipe made of PET having a fiber diameter of 20um or less (wipe retention time: 10 seconds).

5. Baking: baked at the measured temperature of the hotplate 140 ℃ for 15 minutes.

6. UV absorbance measurement: the absorbance difference of UV abs. λ max was measured, and the relative absorbance at the initial absorbance of 100 was recorded (for example, when the initial absorbance was 10 and the absorbance after the treatment was 9, the difference in UV absorbance was calculated as 90%).

TABLE 3

Referring to table 3, it was confirmed that the films of the preparation examples 1-1 to 1-5 and 2-1 to 2-3 showed greater differences in UV absorbance than the films of the comparative preparation examples 1-1, 1-2 and 2-1.

Examples 1 to 1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-corning company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer were spin-coated with B EML-1 to form a film having a thickness of 30nm, and a baking process was performed thereon at 140 ℃ for 10 minutes to form a blue emission layer. The blue emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. The reaction solution is prepared by the method of PEDOT: PSS (Clevios) ^TM HIL 8) was spin-coated with a hole transport layer to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein was a Suicel plus 200 evaporator manufactured by Sunic System Company.

Examples 1-2 to examples 1-7 and comparative examples 1-1 and 1-2

Films were prepared in the same manner as in example 1-1, respectively, except that the ink compositions shown in Table 4 were used instead of ETL-1, B EML-1, or HTL-1, respectively.

Example 2-1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-Corning Company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. Spin-coating the electron injection layer and the electron transport layer with BEML-1 to form a film having a thickness of 30nmAnd a baking process was performed thereon at 140 c for 10 minutes to form a blue emission layer. The blue emitting layer was spin-coated with HTL-3 to form a film having a thickness of 20nm, and UV light (80 mJ/cm) having a wavelength of 254nm was applied ² ) The film is irradiated. Then, a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. With the use of PEDOT: PSS (Clevios) ^TM HIL 8) was spin-coated with a hole transport layer to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein was a Suicel plus 200 evaporator manufactured by Sunic System Company.

Example 2-2 to example 2-5 and comparative example 2-1

Films were prepared in the same manner as in example 2-1, respectively, except that the ink compositions shown in Table 4 were used instead of ETL-1, B EML-1, or HTL-1, respectively.

Example 3-1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-Corning Company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached, to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer were spin-coated with B EML-1 to form a film having a thickness of 30nm, and a baking process was performed thereon at 140 ℃ for 10 minutes to form a blue emission layer. The blue emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. The reaction solution is prepared by the method of PEDOT: PSS (Clevios) ^TM HIL 8) was spin-coated with a hole transport layer to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. The hole injection layer was spin-coated with ETL-1 to form a film having a thickness of 60nm, and a baking process was performed thereon at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer.The electron injection layer and the electron transport layer were spin-coated with B EML-1 to form a film having a thickness of 30nm, and a baking process was performed thereon at 140 ℃ for 10 minutes to form a blue emission layer. The blue emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. With the use of PEDOT: PSS (Clevios) ^TM HIL 8) was spin-coated with a hole transport layer to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein was a Suicel plus 200 evaporator manufactured by Sunic System Company.

Example 3-2 to example 3-7 and comparative example 3-1

Films were prepared in the same manner as in example 3-1, respectively, except that the ink compositions shown in Table 4 were used instead of ETL-1, B EML-1, or HTL-1, respectively.

TABLE 4

	ETL	B EML	HTL
				Examples 1 to 1	ETL-1	B EML-1	HTL-1
Examples 1 to 2	ETL-2	B EML-1	HTL-1
				Examples 1 to 3	ETL-2	B EML-2	HTL-1
Examples 1 to 4	ETL-2	B EML-1	HTL-2
				Examples 1 to 5	ETL-2	B EML-1	HTL-3
Examples 1 to 6	ETL-2	B EML-1	HTL-4
				Examples 1 to 7	ETL-2	B EML-1	HTL-5
Example 2-1	ETL-1	B EML-1	HTL-3
				Examples 2 to 2	ETL-2	B EML-1	HTL-3
Examples 2 to 3	ETL-2	B EML-2	HTL-3
				Examples 2 to 4	ETL-2	B EML-1	HTL-4
Examples 2 to 5	ETL-2	B EML-1	HTL-5
				Example 3-1	ETL-1	B EML-1	HTL-1
Example 3-2	ETL-2	B EML-1	HTL-1
				Examples 3 to 3	ETL-2	B EML-2	HTL-1
Examples 3 to 4	ETL-2	B EML-1	HTL-2
				Examples 3 to 5	ETL-2	B EML-1	HTL-3
Examples 3 to 6	ETL-2	B EML-1	HTL-4
				Examples 3 to 7	ETL-2	B EML-1	HTL-5
Comparative example 1-1	ETL-2	B EML-1	HTL-6
				Comparative examples 1 to 2	ETL-2	B EML-1	HTL-7
Comparative example 2-1	ETL-2	B EML-1	HTL-6
				Comparative example 3-1	ETL-2	B EML-1	HTL-6

Evaluation example 2

With respect to the light emitting devices of example 1-1 to example 1-7, example 2-1 to example 2-5, and example 3-1 to example 3-7, and comparative example 1-1, comparative example 1-2, comparative example 2-1, and comparative example 3-1, the driving voltage, efficiency, and color purity were measured in the following manner, and the results are shown in table 5. Life (T) ₉₅ ) Indicating the initial brightness (at 10 mA/cm) ² ) The time (hr) required for the luminance to reach 95% at 100%.

-color coordinates: power is supplied by a current-voltage meter (ketley SMU 236) and color coordinates are measured using a luminance meter PR 650.

-brightness: power is supplied by a current-voltage meter (ketley SMU 236) and brightness is measured using a brightness meter PR 650.

-efficiency: power was supplied by a current-voltage meter (ketley SMU 236) and efficiency was measured using a luminance meter PR 650.

TABLE 5

Referring to table 5, it was confirmed that the light emitting devices of examples 1-1 to 1-7, 2-1 to 2-5, and 3-1 to 3-7 had excellent light emitting efficiency and life characteristics, compared to the light emitting devices of comparative examples 1-1, 2-1, and 3-1.

Example 4-1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-Corning Company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached, to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. Spin-coating an electron injection layer and an electron transport layer with R EML-1 to form a film having a thickness of 30nm, and performing a baking process thereon at 100 ℃ for 10 minutes to form a red emission layer. The red emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. With the use of PEDOT: PSS (Clevios) ^TM HIL 8) the hole transport layer was spin-coated to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein was a Suicel plus 200 evaporator manufactured by Sunic System Company.

Examples 4-2 to 4-6 and comparative examples 4-1 and 4-2

Films were prepared in the same manner as in example 4-1, respectively, except that the ink compositions shown in Table 6 were used instead of ETL-1, R EML-1, or HTL-1, respectively.

Example 5-1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-Corning Company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached, to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer were spin-coated with R EML-1 to form a film having a thickness of 30nm, and a baking process was performed thereon at 100 ℃ for 10 minutes to form a red emission layer. The red emitting layer was spin-coated with HTL-3 to form a film having a thickness of 20nm, and UV light (80 mJ/cm) having a wavelength of 254nm was applied ² ) The film is irradiated. On which a baking process was performed at 150 c for 10 minutes to form a hole transport layer. The reaction solution is prepared by the method of PEDOT: PSS (Clevios) ^TM HIL 8) the hole transport layer was spin-coated to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein is Sunic System CompaSuicel plus 200 evaporator manufactured by ny.

Example 5-2 to example 5-4 and comparative example 5-1

Films were prepared in the same manner as in example 5-1, respectively, except that the ink compositions shown in Table 6 were used instead of ETL-1, R EML-1, or HTL-1, respectively.

Example 6-1

ITO glass substrate (50 mm. Times.50mm, 15. Omega./cm) was successively subjected to the treatment with distilled water and isopropyl alcohol ² Samsung-Corning Company) and cleaned by exposure to UV ozone for 30 minutes. After cleaning, ETL-1 was spin-coated on a glass substrate to which a transparent electrode line was attached to form a film having a thickness of 60 nm. Then, it was subjected to a baking process at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer were spin-coated with R EML-1 to form a film having a thickness of 30nm, and a baking process was performed thereon at 100 ℃ for 10 minutes to form a red emission layer. The red emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. With the use of PEDOT: PSS (Clevios) ^TM HIL 8) the hole transport layer was spin-coated to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer. The hole injection layer was spin-coated with ETL-1 to form a film having a thickness of 60nm, and a baking process was performed thereon at 120 ℃ for 10 minutes to form an electron injection layer and an electron transport layer. The electron injection layer and the electron transport layer were spin-coated with R EML-1 to form a film having a thickness of 30nm, and a baking treatment was performed thereon at 100 ℃ for 10 minutes to form a red emission layer. The red emission layer was spin-coated with HTL-1 to form a film having a thickness of 20nm, and a baking process was performed thereon at 150 ℃ for 10 minutes to form a hole transport layer. The reaction solution is prepared by the method of PEDOT: PSS (Clevios) ^TM HIL 8) was spin-coated with a hole transport layer to form a film having a thickness of 20nm, and a backing process was performed thereon at 120 ℃ for 30 minutes to form a hole injection layer.

After the obtained glass substrate was mounted on a substrate holder of a vacuum deposition apparatus, al was deposited on the hole injection layer to form an anode having a thickness of 100nm, thereby completing the manufacture of a light-emitting device. The deposition equipment used herein was a Suicel plus 200 evaporator manufactured by Sunic System Company.

Example 6-2 to example 6-6 and comparative example 6-1

Films were prepared in the same manner as in example 6-1, respectively, except that the ink compositions shown in Table 6 were used instead of ETL-1, R EML-1, or HTL-1, respectively.

TABLE 6

	ETL	R EML	HTL
				Example 4-1	ETL-1	R EML-1	HTL-1
Example 4-2	ETL-2	R EML-1	HTL-1
				Examples 4 to 3	ETL-2	R EML-1	HTL-2
Examples 4 to 4	ETL-2	R EML-1	HTL-3
				Examples 4 to 5	ETL-2	R EML-1	HTL-4
Examples 4 to 6	ETL-2	R EML-1	HTL-5
				Example 5-1	ETL-1	R EML-1	HTL-3
Examples 5 and 2	ETL-2	R EML-1	HTL-3
				Examples 5 to 3	ETL-2	R EML-1	HTL-4
Examples 5 to 4	ETL-2	R EML-1	HTL-5
				Example 6-1	ETL-1	R EML-1	HTL-1
Example 6-2	ETL-2	R EML-1	HTL-1
				Examples 6 to 3	ETL-2	R EML-1	HTL-2
Examples 6 to 4	ETL-2	R EML-1	HTL-3
				Examples 6 to 5	ETL-2	R EML-1	HTL-4
Examples 6 to 6	ETL-2	R EML-1	HTL-5
				Comparative example 4-1	ETL-2	R EML-1	HTL-6
Comparative example 4-2	ETL-2	R EML-1	HTL-7
				Comparative example 5-1	ETL-2	R EML-1	HTL-6
Comparative example 6-1	ETL-2	R EML-1	HTL-6

Evaluation example 3

With respect to the light emitting devices of example 4-1 to example 4-6, example 5-1 to example 5-4, and example 6-1 to example 6-6, and comparative example 4-1, comparative example 4-2, comparative example 5-1, and comparative example 6-1, the driving voltage, efficiency, and color purity were measured in the following manner, and the results are shown in table 7. Life (T) ₉₅ ) Indicating the initial brightness (at 10 mA/cm) ² ) The time (hr) required for the luminance to reach 95% at 100%.

TABLE 7

Referring to table 7, it was confirmed that the light emitting devices of examples 4-1 to 4-6, 5-1 to 5-4, and 6-1 to 6-6 had excellent light emitting efficiency and life characteristics, compared to the light emitting devices of comparative examples 4-1, 4-2, 5-1, and 6-1.

According to one or more embodiments, the light emitting device may have high efficiency and long life, and thus may be used to manufacture high-quality electronic apparatuses.

While certain embodiments and implementations have been described herein, other embodiments and variations will be apparent from the description. The inventive concept is therefore not limited to the embodiments but is to be accorded the widest scope consistent with the claims appended hereto and with various obvious modifications and equivalent arrangements which are apparent to those skilled in the art.

Claims

1. A light emitting device comprising:

a substrate;

a cathode disposed on the substrate;

an anode facing the cathode; and

an organic layer disposed between the cathode and the anode and including an emission layer,

wherein the organic layer comprises:

an electron transport region disposed between the emissive layer and the cathode; and

a hole transport region disposed between the emissive layer and the anode,

wherein the hole transport region includes: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof:

formula 1

Formula 1-1

Formula 2

N ₃ -(Ar ₂₁ ) _n21 -(L ₂₁ ) _a21 -(Ar ₂₂ ) _n22 -N ₃

Formula 5

N ₃ -(Ar ₅₁ ) _n51 -(L ₅₁ ) _a51 -(Ar ₅₂ ) _n52 -N ₃

Wherein, in formula 1, formula 1-1, formula 2 and formula 5,

L ₅₁ Is a first repeating unit represented by formula 1,

a11, a21 and a51 are each independently an integer from 1 to 20,

R ₁₁ is a group represented by the formula 1-1, unsubstituted or substituted with at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

i)R ₁₂ is a binding site to an adjacent atom in formula 1, and R ₁₃ Is hydrogen, or ii) R ₁₂ Is hydrogen, and R ₁₃ Are binding sites to adjacent atoms in formula 1,

* And each indicates a binding site to an adjacent atom,

R _10a comprises the following steps:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

C ₁ -C ₆₀ alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl or C ₁ -C ₆₀ Alkoxy, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy group, C ₆ -C ₆₀ Arylthio, -Si (Q) ₁₁ )(Q ₁₂ )(Q ₁₃ )、-N(Q ₁₁ )(Q ₁₂ )、-B(Q ₁₁ )(Q ₁₂ )、-C(＝O)(Q ₁₁ )、-S(＝O) ₂ (Q ₁₁ )、-P(＝O)(Q ₁₁ )(Q ₁₂ ) Or any combination thereof;

C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical or C ₆ -C ₆₀ Arylthio groups, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₁ -C ₆₀ Alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy radical, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio, -Si (Q) ₂₁ )(Q ₂₂ )(Q ₂₃ )、-N(Q ₂₁ )(Q ₂₂ )、-B(Q ₂₁ )(Q ₂₂ )、-C(＝O)(Q ₂₁ )、-S(＝O) ₂ (Q ₂₁ )、-P(＝O)(Q ₂₁ )(Q ₂₂ ) Or any combination thereof; or

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ ) or-P (= O) (Q) ₃₁ )(Q ₃₂ ) And is and

Q ₁ to Q ₃ 、Q ₁₁ To Q ₁₃ 、Q ₂₁ To Q ₂₃ And Q ₃₁ To Q ₃₃ Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c ₁ -C ₆₀ An alkyl group; c ₂ -C ₆₀ An alkenyl group; c ₂ -C ₆₀ Alkynyl; c ₁ -C ₆₀ An alkoxy group; or C ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ Heterocyclic radicals, each of which is unsubstituted or deuterated, -F, cyano, C ₁ -C ₆₀ Alkyl radical, C ₁ -C ₆₀ Alkoxy, phenyl, biphenyl, or any combination thereof.

2. The light-emitting device according to claim 1, wherein Ar ₁₁ To Ar ₁₃ Each independently is:

a single bond, phenylene, naphthalene or fluorene; or

3. The light-emitting device according to claim 1, wherein Ar ₂₁ And Ar ₂₂ Each independently is:

phenylene or naphthalene; or

Phenylene or naphthalene, each of which is deuterium, -F or C ₁ -C ₁₀ Alkyl substitution.

4. The light-emitting device according to claim 1, wherein Ar ₁₁ To Ar ₁₃ Each independently a single bond or a group represented by one of formula 1A-1 to formula 1A-13 and formula 1B-1 to formula 1B-10:

wherein, in formulae 1A-1 to 1A-13 and formulae 1B-1 to 1B-10,

R _1c and R _1d Each independently of the others is hydrogen, deuterium, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

* And each indicates a binding site to an adjacent atom, and

R _10a as claimed in claim 1.

5. The light-emitting device according to claim 1, wherein Ar ₂₁ And Ar ₂₂ Each independently is a group represented by one of formulae 2A-1 to 2A-13:

wherein, in the formulae 2A-1 to 2A-13,

Z ₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano or nitro,

b11 is an integer from 1 to 4,

b12 is an integer from 1 to 6, and

* And each indicates a binding site to an adjacent atom.

6. The light-emitting device according to claim 1, wherein the compound represented by formula 1 (L) ₁₁ ) _a11 The moiety represented is a group represented by formula 1L:

wherein, in the formula 1L,

n1L is an integer from 0 to 10,

Z _1L is hydrogen, deuterium, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenyl, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynyl, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkoxy radical, aminoSubstituted or by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Heterocyclic radical, unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ Aryloxy, or unsubstituted or substituted by at least one R _10a Substituted C ₆ -C ₆₀ An arylthio group, and

R _10a as claimed in claim 1.

7. The light emitting device of claim 1, wherein L ₂₁ Is a single bond, — C (R) _1a )(R _1b )-*'、*-C(R _1a )＝*'、*＝C(R _1a )-*'、*-C(R _1a )＝C(R _1b ) -, - (= O) -, or-',

* And each indicates a binding site to an adjacent atom, and

R _1a and R _1b As described in claim 1, respectively.

8. The light emitting device of claim 1, wherein R ₁₁ Is a group represented by formula 1-1.

9. The light emitting device of claim 1, wherein R ₁₄ 、R ₁₅ 、R _1a And R _1b Each independently is:

phenyl or naphthyl, each of which is unsubstituted or substituted by deuterium, -F, -Cl, -Br, -I, -CD ₃ 、-CD ₂ H、-CDH ₂ 、-CF ₃ 、-CF ₂ H、-CFH ₂ 、C ₁ -C ₂₀ Alkyl radical, C ₁ -C ₂₀ Alkoxy, or any combination thereof.

10. The light-emitting device according to claim 1, wherein the electron-transporting region includes a third compound represented by formula 3:

formula 3

M _p O _q

Wherein, in the formula 3,

m is Zn, ti, zr, sn, W, ta, ni, mo, cu or V, and

p and q are each independently integers from 1 to 5.

11. The light-emitting device according to claim 10, wherein the third compound is represented by formula 3-1:

formula 3-1

Zn _(1-r) M' _r O

Wherein, in the formula 3-1,

m' is Mg, co, ni, zr, mn, sn, Y, al or any combination thereof, and

r is a number greater than 0 and equal to or less than 0.5.

12. A light emitting device comprising:

a substrate;

a cathode disposed on the substrate;

an anode facing the cathode;

x light emitting units disposed between the cathode and the anode; and

wherein x is an integer of 2 or more,

each of the x light emitting units includes an electron transport region, an emission layer, and a hole transport region sequentially arranged from the cathode, and

the hole transport region includes: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof:

formula 1

Formula 1-1

Formula 2

N ₃ -(Ar ₂₁ ) _n21 -(L ₂₁ ) _a21 -(Ar ₂₂ ) _n22 -N ₃

Formula 5

N ₃ -(Ar ₅₁ ) _n51 -(L ₅₁ ) _a51 -(Ar ₅₂ ) _n52 -N ₃

Wherein, in formula 1, formula 1-1, formula 2 and formula 5,

L ₅₁ Is a first repeating unit represented by formula 1,

a11, a21 and a51 are each independently an integer from 1 to 20,

* And each indicates a binding site to an adjacent atom,

R _10a comprises the following steps:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

C ₁ -C ₆₀ alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl or C ₁ -C ₆₀ Alkoxy, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy group, C ₆ -C ₆₀ Arylthio, -Si (Q) ₁₁ )(Q ₁₂ )(Q ₁₃ )、-N(Q ₁₁ )(Q ₁₂ )、-B(Q ₁₁ )(Q ₁₂ )、-C(＝O)(Q ₁₁ )、-S(＝O) ₂ (Q ₁₁ )、-P(＝O)(Q ₁₁ )(Q ₁₂ ) Or any combination thereof;

C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical or C ₆ -C ₆₀ Arylthio groups, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₁ -C ₆₀ Alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy radical, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy group, C ₆ -C ₆₀ Arylthio, -Si (Q) ₂₁ )(Q ₂₂ )(Q ₂₃ )、-N(Q ₂₁ )(Q ₂₂ )、-B(Q ₂₁ )(Q ₂₂ )、-C(＝O)(Q ₂₁ )、-S(＝O) ₂ (Q ₂₁ )、-P(＝O)(Q ₂₁ )(Q ₂₂ ) Or any combination thereof; or

13. The light emitting device of claim 12, wherein x is 2 or 3.

14. The light-emitting device according to claim 12, wherein each of the x-1 charge generation layers comprises a hole transport material.

15. The light-emitting device according to claim 12, wherein each of the x-1 charge generation layers comprises a fourth compound represented by formula 4:

formula 4

Wherein, in the formula 4,

e is boron (B), al, ga, in or Tl,

R ₄₁ to R ₄₄ Each independently is unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic radicalsThe radical being either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

R _10a comprises the following steps:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

C ₁ -C ₆₀ alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl or C ₁ -C ₆₀ Alkoxy, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio, -Si (Q) ₁₁ )(Q ₁₂ )(Q ₁₃ )、-N(Q ₁₁ )(Q ₁₂ )、-B(Q ₁₁ )(Q ₁₂ )、-C(＝O)(Q ₁₁ )、-S(＝O) ₂ (Q ₁₁ )、-P(＝O)(Q ₁₁ )(Q ₁₂ ) Or any combination thereof;

C ₃ -C ₆₀ carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical or C ₆ -C ₆₀ Arylthio groups, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C ₁ -C ₆₀ Alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl, C ₁ -C ₆₀ Alkoxy radical, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio, -Si (Q) ₂₁ )(Q ₂₂ )(Q ₂₃ )、-N(Q ₂₁ )(Q ₂₂ )、-B(Q ₂₁ )(Q ₂₂ )、-C(＝O)(Q ₂₁ )、-S(＝O) ₂ (Q ₂₁ )、-P(＝O)(Q ₂₁ )(Q ₂₂ ) Or any combination thereof; or

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ )、-N(Q ₃₁ )(Q ₃₂ )、-B(Q ₃₁ )(Q ₃₂ )、-C(＝O)(Q ₃₁ )、-S(＝O) ₂ (Q ₃₁ ) or-P (= O) (Q) ₃₁ )(Q ₃₂ ) And are each and every

Q ₁ To Q ₃ 、Q ₁₁ To Q ₁₃ 、Q ₂₁ To Q ₂₃ And Q ₃₁ To Q ₃₃ Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c ₁ -C ₆₀ An alkyl group; c ₂ -C ₆₀ An alkenyl group; c ₂ -C ₆₀ An alkynyl group; c ₁ -C ₆₀ An alkoxy group; or C ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ Heterocyclic radicals, each of which is unsubstituted or deuterated, -F, cyano, C ₁ -C ₆₀ Alkyl radical, C ₁ -C ₆₀ Alkoxy, phenyl, biphenyl, or any combination thereof.

16. A method of manufacturing a light emitting device, the method comprising:

forming a cathode on a substrate;

forming a first organic layer between the cathode and the anode;

forming a second organic layer between the anode and the first organic layer; and

forming a third organic layer between the second organic layer and the anode,

wherein forming the third organic layer is performed by a solution process using a composition comprising: a first compound comprising a first repeating unit represented by formula 1, a second compound represented by formula 2, a fifth compound represented by formula 5, or any combination thereof:

formula 1

Formula 1-1

Formula 2

N ₃ -(Ar ₂₁ ) _n21 -(L ₂₁ ) _a21 -(Ar ₂₂ ) _n22 -N ₃

Formula 5

N ₃ -(Ar ₅₁ ) _n51 -(L ₅₄ ) _a51 -(Ar ₅₂ ) _n52 -N ₃

Wherein, in formula 1, formula 1-1, formula 2 and formula 5,

Ar ₁₁ to Ar ₁₃ 、Ar ₂₁ 、Ar ₂₂ 、Ar ₅₁ And Ar ₅₂ Each independently of the others being a single bond, unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ Alkylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkenylene, unsubstituted or substituted by at least one R _10a Substituted C ₂ -C ₆₀ Alkynylene, unsubstituted or substituted by at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, or unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

L ₅₁ Is a first repeating unit represented by formula 1,

a11, a21 and a51 are each independently an integer from 1 to 20,

R ₁₁ is a group represented by the formula 1-1, unsubstituted or substituted with at least one R _10a Substituted C ₃ -C ₆₀ Carbocyclic group, either unsubstituted or substituted by at least one R _10a Substituted C ₁ -C ₆₀ A heterocyclic group,

* And each indicates a binding site to an adjacent atom,

R _10a comprises the following steps:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano or nitro;

C ₁ -C ₆₀ alkyl radical, C ₂ -C ₆₀ Alkenyl radical, C ₂ -C ₆₀ Alkynyl or C ₁ -C ₆₀ Alkoxy, each of which is unsubstituted or substituted by: deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitroBase, C ₃ -C ₆₀ Carbocyclic group, C ₁ -C ₆₀ Heterocyclic group, C ₆ -C ₆₀ Aryloxy radical, C ₆ -C ₆₀ Arylthio, -Si (Q) ₁₁ )(Q ₁₂ )(Q ₁₃ )、-N(Q ₁₁ )(Q ₁₂ )、-B(Q ₁₁ )(Q ₁₂ )、-C(＝O)(Q ₁₁ )、-S(＝O) ₂ (Q ₁₁ )、-P(＝O)(Q ₁₁ )(Q ₁₂ ) Or any combination thereof;

Q ₁ To Q ₃ 、Q ₁₁ To Q ₁₃ 、Q ₂₁ To Q ₂₃ And Q ₃₁ To Q ₃₃ Each independently is: hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; c ₁ -C ₆₀ An alkyl group; c ₂ -C ₆₀ An alkenyl group; c ₂ -C ₆₀ An alkynyl group; c ₁ -C ₆₀ An alkoxy group; or C ₃ -C ₆₀ Carbocyclic group or C ₁ -C ₆₀ Heterocyclic radicals, each of which is unsubstituted or substituted by deuterium, -F, cyano, C ₁ -C ₆₀ Alkyl radical, C ₁ -C ₆₀ Alkoxy, phenyl, biphenyl, or any combination thereof.

17. The method of claim 16, wherein forming the first organic layer is performed by a solution method using a composition comprising a third compound represented by formula 3:

formula 3

M _p O _q

Wherein, in the formula 3,

m is Zn, ti, zr, sn, W, ta, ni, mo, cu or V, and

p and q are each independently integers from 1 to 5.

18. The method of claim 16, wherein forming the first organic layer, forming the second organic layer, and forming the third organic layer each comprise evaporating a solvent.

19. The method of claim 18, wherein evaporating the solvent is performed at a temperature in a range of 110 ℃ to 180 ℃.

20. The method of claim 18, wherein the method further comprises irradiating the composition with UV prior to evaporating the solvent.